Diastereoselective Conjugate Addition of Organocuprates to Chiral N-Enoyl Oxazolidinethiones

被引：18

作者：

Sabala, Rocio ^{[2
]}

Hernandez-Garcia, Luis ^{[1
]}

Ortiz, Aurelio ^{[2
]}

Romero, Moises ^{[1
]}

Olivo, Horacio F. ^{[1
]}

机构：

[1] Univ Iowa, Div Med & Nat Prod Chem, Iowa City, IA 52242 USA

[2] Benemerita Univ Autonoma Puebla, Fac Ciencias Quim, Puebla 72570, Mexico

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 19期

关键词：

INTRAMOLECULAR SULFUR TRANSFER; ASYMMETRIC MICHAEL ADDITION; SUBSTITUTION-REACTIONS; ACID-DERIVATIVES; CARBOXYLIC-ACIDS; REAGENTS; THIAZOLIDINETHIONES; ENOYLTHIOAMIDES; OXAZOLIDINONES; 1,4-ADDITION;

D O I：

10.1021/ol101687e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of organocuprates, generated in situ using an excess of a 1:2 mixture of CuI center dot DMS and Grignard reagent, to N-enoyl oxazolidinethiones in the presence of excess TMSI gave preferentially the anti diastereomer where the addition took place when the conformation of the substrate was syn-s-cis. The reaction was investigated with indene-based and three different phenyl glycine derived oxazolidinethiones.

引用

页码：4268 / 4270

页数：3

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