H-Bond-Directing Organocatalyst for Enantioselective [4+2] Cycloadditions via Dienamine Catalysis

被引：62

作者：

Wang, Shoulei ^{[1
]}

Rodriguez-Escrich, Carles ^{[1
]}

Pericas, Miguel A. ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Av Paisos Catalans 16, Tarragona 43007, Spain

[2] Univ Barcelona, Dept Quim Inorgan, Barcelona 08080, Spain

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 03期

关键词：

DIELS-ALDER REACTION; MICHAEL ADDITION; ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; UNSATURATED PYRAZOLONES; TERTIARY STEREOCENTERS; CARBONYL-COMPOUNDS; DERIVATIVES; SPIROPYRAZOLONES; ACTIVATION;

D O I：

10.1021/acs.orglett.5b03575

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, highly regio- and stereoselective [4 + 2] cycloaddition reaction to generate tetrahydropyranopyrazole frameworks has been developed. To this end, a dienamine-based catalytic strategy that relies on the H-bond-directing effect of the hydroxy group of a dinaphthylprolinol-type aminocatalyst has been used. This enables the synthesis of multifunctionalized heterocyclic derivatives with three contiguous stereocenters in good yields and excellent enantioselectivities.

引用

页码：556 / 559

页数：4

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