Regio- and Diastereoselective Conjugate Addition of Grignard Reagents to Chiral Fluoroalkyl α,β-Unsaturated N-tert-Butanesulfinyl Ketimines: Synthesis of Optically Active Fluorinated Enamines and Derivatives

被引：0

作者：

Ma, Wen-Jiang ^{[1
]}

Liu, Peng ^{[1
]}

Liao, Tian-Ming ^{[1
]}

Gao, Yu-Ning ^{[1
]}

Bian, Ming ^{[1
]}

Liu, Jin-Tao ^{[2
]}

Wu, Fanhong ^{[1
]}

Chen, Hui-Yu ^{[1
]}

Liu, Zhen-Jiang ^{[1
,2
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Haiquan Rd, Shanghai 201418, Peoples R China

[2] Chinese Acad Sci, Key Lab Organofluorine Chem, Shanghai Inst Organ Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Conjugate addition; Fluorinated enamines; N-tert-Butanesulfinyl ketimine; Regioselective; Diastereoselective; ASYMMETRIC-SYNTHESIS; IMINES;

D O I：

10.1002/adsc.202300983

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A regio- and diastereoselective conjugate addition reaction of Grignard reagents to fluoroalkyl alpha,beta-unsaturated N-tert-butanesulfinyl ketimines was disclosed. A range of different fluoroalkyls and Grignard reagents were well tolerated, giving up to 99% diastereomeric and regioisomeric ratios. This reaction provided a straightforward method for the synthesis of a variety of enantiomerically enriched alpha-fluorinated enamines and derivatives which are difficult to achieve with other methods.

引用

页码：414 / 419

页数：6

共 22 条

[21] Diastereoselective Addition of PhSCF2SiMe3 to Chiral N-tert- Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles
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[22] ASYMMETRIC CONJUGATE ADDITION TO UNSATURATED CHIRAL AMIDO ALCOHOLS USING GRIGNARD-REAGENTS COORDINATED WITH TERTIARY-AMINES OR DBU - PREPARATION OF OPTICALLY-ACTIVE 3-SUBSTITUTED CARBOXYLIC-ACIDS AND (S)-(-)-CITRONELLOL
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MACHIDA, H
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