Tetrahydropyran-Based Hybrid Dipeptides as Asymmetric Catalysts for Michael Addition of Aldehydes to β-Nitrostyrenes

被引：16

作者：

Borges-Gonzalez, Jorge ^{[1
]}

Feher-Voelger, Andres ^{[1
]}

Pinacho Crisostomo, Fernando ^{[1
,2
]}

Morales, Ezequiel Q. ^{[1
]}

Martin, Tomas ^{[1
,2
]}

机构：

[1] CSIC, Inst Prod Nat & Agrobiol, Avda Astrofis Francisco Sanchez 3, San Cristobal la Laguna 38206, Sc De Tenerife, Spain

[2] CIBICAN, Inst Univ Bioorgan Antonio Gonzalez, Avda Astrofis Francisco Sanchez 2, San Cristobal la Laguna 38206, Sc De Tenerife, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 04期

关键词：

aldehydes; asymmetric catalysis; Michael addition; organocatalysis; peptides; CONJUGATE ADDITION; CONFORMATIONAL-ANALYSIS; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; EFFICIENT ORGANOCATALYSTS; 1,4-ADDITION REACTIONS; FORCE-FIELD; KETONES; PEPTIDES; NITROOLEFINS; NITROALKENES;

D O I：

10.1002/adsc.201601193

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new series of hybrid dipeptide-like organocatalysts based on pyranoid E- or -amino acids and proline have been prepared for the asymmetric Michael addition of aldehydes to -nitrostyrenes. The reaction proceeds under mild conditions to afford a wide range of -nitroaldehydes with up to 98% yield and up to 96% ee. These dipeptides are bifunctional organocatalysts, with a proline at the N-terminus and a carboxylic acid at the C-terminus. The tetrahydropyran unit embedded in the E- or -amino acid induces a well-defined conformation that is responsible for the catalysis. These dipeptides represent a new type of organocatalyst with a large number of possibilities to modulate their reactivity and selectivity.

引用

页码：576 / 583

页数：8

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