Asymmetric Synthesis of Octahydroindoles via a Domino Robinson Annulation/5-Endo Intramolecular Aza-Michael Reaction

被引：15

作者：

Parra, Claudio ^{[1
]}

Bosch, Caroline ^{[1
]}

Gomez-Bengoa, Enrique ^{[2
]}

Bonjoch, Josep ^{[1
]}

Bradshaw, Ben ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, IBUB, Lab Quim Organ, Av Joan 23 S-N, E-08028 Barcelona, Spain

[2] Univ Basque Country, Dept Quim Organ 1, Manuel Lardizabal 3, San Sebastian 20018, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 21期

关键词：

ENANTIOSELECTIVE SYNTHESIS; ALKALOIDS; ORGANOCATALYSIS; CYCLIZATION; ALKYLATION; ACTIVATION; CORE; ACID;

D O I：

10.1021/acs.joc.6b01568

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward, two-step asymmetric synthesis of octahydroindoles has been developed on the basis of two complementary strategies: (i) an organocatalyzed Michael reaction followed by a tandem Robinson-aza-Michael double cyclization catalyzed by PS-BEMP, and (ii) a diastereoselective cyclization, which formally constitutes a remote 1,6 asymmetric induction mediated by PS-BEMP. This allowed the construction of complex octahydroindoles with up to four stereocenters, excellent enantioselectivities (up to 95% ee), and complete diastereoselective control in a single-pot operation. DFT calculations were performed to understand the origin of this effect.

引用

页码：10172 / 10179

页数：8

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