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

被引：69

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

页码：5357 / 5360

页数：4

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