Highly stereoselective tandem aza-michael addition-enolate protonation to form partially modified retropeptide mimetics incorporating a trifluoroalanine surrogate

被引：81

作者：

Sani, M

Bruché, L

Chiva, G

Fustero, S

Piera, J

Volonterio, A

Zanda, M

机构：

[1] CNR, ICRM, Sezione A Quil, I-20131 Milan, Italy

[2] Politecn Milan, Dipartimento Chim Mat & Ingn Chim Giulio Natta, I-20131 Milan, Italy

[3] Univ Valencia, Fac Farm, Dept Quim Organ, E-46100 Valencia, Spain

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 18期

关键词：

diastereoselectivity; Michael addition; peptidomimetics; protonation; solvent effects;

D O I：

10.1002/anie.200250711

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Fine-tuning of key reaction parameters, such as the solvent and the base used, led to a dramatic improvement in d.r. (from ≈1:1 to 38:1) in a tandem aza-Michael addition-enolate protonation sequence. Thus, the reaction of α-amino ester nucleophiles 1 with N-(α-trifiuoromethyl)acryloyl-α-amino ester acceptors 2 produced an array of partially modified retropeptide mimetics 3 with good to excellent stereocontrol (R, R1, R2, X, X1 = alkyl).

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收藏

页码：2060 / 2063

页数：4

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