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
收藏
页码：4268 / 4270
页数：3
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