Stereoselective nucleophilic addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to chiral cyclic nitrones: Asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines

Stereoselective nucleophilic addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to chiral cyclic nitrones: Asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Fluoride-catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group ("PhSCF2") generated from PhSCF2SiMe3 to nitrones was accomplished in satisfactory yields. High diastereoselectivities were observed with chiral polyo...

Full description

Saved in:

Bibliographic Details
Main Authors:	Korkit Korvorapun, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr
Other Authors:	Mahidol University
Format:	Article
Published:	2018
Subjects:	Chemistry
Online Access:	https://repository.li.mahidol.ac.th/handle/123456789/35763
Tags:	Add Tag No Tags, Be the first to tag this record!

Similar Items

Synthesis of gem -difluoromethylenated compounds employing α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF<inf>2</inf>SiMe<inf>3</inf>) as a gem -difluoromethylene building block
by: Darunee Soorukram, et al.
Published: (2018)

Synthesis of gem-difluoromethylenated spiro-γ-butyrolactones by employing PhSCF<inf>2</inf>Si(CH<inf>3</inf>)<inf>3</inf>as a gem-difluoromethylenating agent
by: Adisak Chatupheeraphat, et al.
Published: (2018)

Nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl compounds with PhSCF<inf>2</inf>H in the presence of a phosphazene as a base
by: Teerachai Punirun, et al.
Published: (2018)

Fluoride-Catalyzed Nucleophilic Addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to Isatins: Synthesis of 3-(1′,1′-Difluoroalkyl)-3-hydroxyindolin-2-ones
by: Sirisuk Keereewan, et al.
Published: (2019)

Diastereoselective Addition of PhSCF<inf>2</inf>SiMe<inf>3</inf>to Chiral N- tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles
by: Keereewan S.
Published: (2023)

Fluoride-catalyzed nucleophilic addition of PhSCF<inf>2</inf>SiMe <inf>3</inf> to anhydrides: Synthesis of γ-difluoromethylated γ-lactams
by: Vannapha Pharikronburee, et al.
Published: (2018)

Synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones using PhSCF<inf>2</inf>SiMe<inf>3</inf>as a difluoromethylating agent
by: Arisara Issaree, et al.
Published: (2018)

Synthesis of C<inf>2</inf>-Symmetric gem-Difluoromethylenated Angular Triquinanes
by: Watcharaporn Thaharn, et al.
Published: (2019)

Asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines
by: Watcharaporn Thaharn, et al.
Published: (2018)

Stereoselective Synthesis of gem-Difluoromethylenated Linear Azatriquinanes
by: Chonticha Masusai, et al.
Published: (2019)

Fluoride-catalyzed addition of PhSCF2SiMe3 to N-substituted cyclic imides followed by radical cyclization: General synthetic strategy of gem-difluoromethylenated 1-azabicyclic compounds
by: Teerawut Bootwicha, et al.
Published: (2018)

α,α-Difluoro-α-phenylsulfanyl-α- trimethylsilylmethane as "cF<inf>2</inf><sup>-</sup>" synthetic building block for the preparation of gem-difluoromethylenated cyclopentanols
by: Krisana Peewasan, et al.
Published: (2018)

A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
by: Chonticha Masusai, et al.
Published: (2018)

Synthesis of aromatic functionalized cage-rearranged silsesquioxanes (T<inf>8</inf>, T<inf>10</inf>, and T<inf>12</inf>) via nucleophilic substitution reactions
by: Supansa Chimjarn, et al.
Published: (2018)

Synthesis of 3-((trifluoromethyl)thio)indoles via trifluoromethylthiolation of 2-alkynyl azidoarenes with AgSCF<inf>3</inf>
by: Jongkonporn Phetcharawetch, et al.
Published: (2022)

Unprecedented Reactivity of AgSCF<inf>3</inf> with o-Isocyanobiaryls: Synthetic and Mechanistic Insight
by: Phetcharawetch J.
Published: (2023)

Comparative study of a GEM-based fast neutron detector using<sup>4</sup>HE/CO<inf>2</inf>and<sup>4</sup>HE/CO<inf>2</inf>/C<inf>4</inf>H<inf>10</inf>gas mixtures
by: Kiadtisak Saenboonruang, et al.
Published: (2018)

Comparative study of a GEM-based fast neutron detector using<sup>4</sup>HE/CO<inf>2</inf>and<sup>4</sup>HE/CO<inf>2</inf>/C<inf>4</inf>H<inf>10</inf>gas mixtures
by: Kiadtisak Saenboonruang, et al.
Published: (2018)

Synthesis of gem -difluoromethylenated polycyclic cage compounds
by: Chonticha Masusai, et al.
Published: (2018)

Synthesis of gem-difluoromethylenated bicyclo[ m.n. 0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones
by: Teerachai Punirun, et al.
Published: (2018)

Lead substitution in the bismuth superconductors (Bi,Pb)<inf>4</inf>Sr<inf>4</inf>Ca<inf>2</inf>Cu<inf>4</inf>O<inf>y</inf>and (Bi,Pb)<inf>4</inf>Sr<inf>3</inf>Ca<inf>3</inf>Cu<inf>4</inf>O<inf>y</inf>
by: I. M. Tang, et al.
Published: (2018)

A series of new microporous lanthanide frameworks [Ln(C<inf>8</inf>H<inf>3</inf>NO<inf>6</inf>)(L)<inf>0.5</inf>(H<inf>2</inf>O)]·3H<inf>2</inf>O (Ln = Pr, Nd, Sm and Gd, and L = C<inf>8</inf>H<inf>4</inf>O<inf>4</inf>or C<inf>8</inf>H<inf>4</inf>O<inf>4</inf>/C<inf>8</inf>H<inf>3</inf>NO<inf>6</inf>): Syntheses, characterization and photoluminescence properties
by: Kitt Panyarat, et al.
Published: (2018)

A series of new microporous lanthanide frameworks [Ln(C<inf>8</inf>H<inf>3</inf>NO<inf>6</inf>)(L)<inf>0.5</inf>(H<inf>2</inf>O)]·3H<inf>2</inf>O (Ln = Pr, Nd, Sm and Gd, and L = C<inf>8</inf>H<inf>4</inf>O<inf>4</inf>or C<inf>8</inf>H<inf>4</inf>O<inf>4</inf>/C<inf>8</inf>H<inf>3</inf>NO<inf>6</inf>): Syntheses, characterization and photoluminescence properties
by: Kitt Panyarat, et al.
Published: (2018)

Microwave assisted crystal growth of a new organic-decavanadate assembly: [V<inf>10</inf>O<inf>27</inf>(OH)] · 2(C<inf>6</inf>N<inf>2</inf>H<inf>14</inf>) · (C<inf>6</inf>N<inf>2</inf>H<inf>13</inf>) · (C<inf>6</inf>N<inf>2</inf>H<inf>12</inf>) · 2H<inf>2</inf>O
by: Bunlawee Yotnoi, et al.
Published: (2018)

Microwave assisted crystal growth of a new organic-decavanadate assembly: [V<inf>10</inf>O<inf>27</inf>(OH)] · 2(C<inf>6</inf>N<inf>2</inf>H<inf>14</inf>) · (C<inf>6</inf>N<inf>2</inf>H<inf>13</inf>) · (C<inf>6</inf>N<inf>2</inf>H<inf>12</inf>) · 2H<inf>2</inf>O
by: Bunlawee Yotnoi, et al.
Published: (2018)

XANES and luminescence studies of M<inf>2</inf>O<inf>3</inf>-CaO-SiO<inf>2</inf>-B<inf>2</inf>O<inf>3</inf> (M<inf>2</inf>O<inf>3</inf> = Y<inf>2</inf>O<inf>3</inf> and La<inf>2</inf>O<inf>3</inf>) glasses doped with Dy<sup>3+</sup> ions
by: Siriprapa Kaewjaeng, et al.
Published: (2018)

Thermoelectric properties of YBa<inf>2</inf>Cu<inf>3</inf>O<inf>7−</inf><inf>x</inf>-Na<inf>y</inf>CoO<inf>2</inf> segmented oxide ceramics
by: Pimpilai Wannasut, et al.
Published: (2018)

Effect of Bi<inf>2</inf>O<inf>3</inf> content on properties of (Na <inf>2</inf>O, K<inf>2</inf>O)-SiO<inf>2</inf>-CaO-Al<inf>2</inf>O <inf>3</inf>-B<inf>2</inf>O<inf>3</inf> glass system
by: P. Dararutana, et al.
Published: (2018)

Effect of Bi<inf>2</inf>O<inf>3</inf> content on properties of (Na <inf>2</inf>O, K<inf>2</inf>O)-SiO<inf>2</inf>-CaO-Al<inf>2</inf>O <inf>3</inf>-B<inf>2</inf>O<inf>3</inf> glass system
by: P. Dararutana, et al.
Published: (2018)

Fabrication and characterization of BaTiO<inf>3</inf>-Ni<inf>0.8</inf>Zn<inf>0.2</inf>Fe<inf>2</inf>O<inf>4</inf>-B<inf>2</inf>O<inf>3</inf>-Na<inf>2</inf>O-SiO<inf>2</inf>multiferroic glass ceramics
by: Pratthana Intawin, et al.
Published: (2018)

Fabrication and characterization of BaTiO<inf>3</inf>-Ni<inf>0.8</inf>Zn<inf>0.2</inf>Fe<inf>2</inf>O<inf>4</inf>-B<inf>2</inf>O<inf>3</inf>-Na<inf>2</inf>O-SiO<inf>2</inf> multiferroic glass ceramics
by: Intawin P., et al.
Published: (2017)

Dielectric properties of Ba<inf>1-</inf><inf>x</inf>Sr<inf>x</inf>(Fe<inf>0.5</inf>Ta<inf>0.5</inf>)O<inf>3</inf>giant dielectric ceramics
by: L. Tawee, et al.
Published: (2018)

Dielectric properties of Ba<inf>1-</inf><inf>x</inf>Sr<inf>x</inf>(Fe<inf>0.5</inf>Ta<inf>0.5</inf>)O<inf>3</inf>giant dielectric ceramics
by: L. Tawee, et al.
Published: (2018)

Dielectric properties of Ba<inf>1-</inf><inf>x</inf>Sr<inf>x</inf>(Fe<inf>0.5</inf>Ta<inf>0.5</inf>)O<inf>3</inf> giant dielectric ceramics
by: Tawee L., et al.
Published: (2017)

Thermoelectric Properties of YBa <inf>2</inf> Cu <inf>3</inf> O <inf>7−x</inf> -Ca <inf>3</inf> Co <inf>4</inf> O <inf>9</inf> Segmented Oxide Ceramic
by: Pimpilai Wannasut, et al.
Published: (2019)

Sinterbility of (Bi<inf>1-x</inf>La<inf>x</inf>Ti<inf>3</inf>O<inf>12</inf> ceramics
by: P. Siriprapa, et al.
Published: (2018)

The tripartite Ramsey numbers r<inf>t</inf>(C<inf>4</inf>;2) and r<inf>t</inf>(C<inf>4</inf>;3)
by: S. Buada, et al.
Published: (2018)

Difluorophenylsulfanylmethyl radical and difluoromethylene diradical synthons: gem-difluoromethylene building block
by: Vichai Reutrakul, et al.
Published: (2018)

Phase Development and Dielectric, Ferroelectric and Piezoelectric Properties of Pb(Mg<inf>1/3</inf>Nb<inf>2/3</inf>)<inf>0.9</inf>Ti<inf>0.1</inf>O<inf>3</inf>-Bi<inf>0.5</inf>(Na<inf>0.74</inf>K<inf>0.26</inf>)<inf>0.5</inf>TiO<inf>3</inf>Ceramics
by: Methee Promsawat, et al.
Published: (2018)

Phase Development and Dielectric, Ferroelectric and Piezoelectric Properties of Pb(Mg<inf>1/3</inf>Nb<inf>2/3</inf>)<inf>0.9</inf>Ti<inf>0.1</inf>O<inf>3</inf>-Bi<inf>0.5</inf>(Na<inf>0.74</inf>K<inf>0.26</inf>)<inf>0.5</inf>TiO<inf>3</inf>Ceramics
by: Methee Promsawat, et al.
Published: (2018)