Facile Approach to Optically Active α-Alkylidene-β-amino Esters by Thermal Overman Rearrangement

被引：19
作者：
Lee, Sung Il [3 ]
Moon, Soon Young [3 ]
Hwang, Geum-Sook [1 ,2 ]
Ryu, Do Hyun [3 ]
机构：
[1] Chungnam Natl Univ, Korea Basic Sci Inst, Seoul 136713, South Korea
[2] Chungnam Natl Univ, Grad Sch Analyt Sci & Technol, Seoul 136713, South Korea
[3] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 14期
关键词：
BAYLIS-HILLMAN ESTERS; CATALYTIC ASYMMETRIC REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; SIGMATROPIC REARRANGEMENT; ALLYLIC AMINES; ACID; HYDROXY; TRANSPOSITION; ADDUCTS;
D O I：
10.1021/ol1011746
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient synthetic method for enantioenriched (E)-alpha-alkylidene-beta-amino esters has been developed through thermal Overman rearrangement. Readily accessible (Z)-beta-branched Morita-Baylis-Hillman esters serve as chiral pool precursors. Thermal rearrangement proceeded through a concerted pseudopericyclic transition state to produce (E)-stereoselective products. We expanded the synthetic utilities of alpha-alkylidene-beta-amino esters via preparation of alpha-alkylidene-beta-lactam derivatives.
引用
收藏
页码：3234 / 3237
页数：4
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