β-isocupreidine-catalyzed baylis -: Hillman reaction of chiral N-boc-α-amino aldehydes

被引：67
|
作者：
Nakano, Ayako [1 ]
Takahashi, Keisuke [1 ]
Ishihara, Jun [1 ]
Hatakeyama, Susumi [1 ]
机构：
[1] Nagasaki Univ, Grad Sch Biomed Sci, Nagasaki 8528521, Japan
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 23期
关键词：
D O I：
10.1021/ol0622561
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] beta-Isocupreidine (beta-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-alpha-amino aldehydes and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, L-substrates show excellent syn selectivity and high reactivity in contrast to D-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity.
引用
收藏
页码：5357 / 5360
页数：4
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