Enantioselective Synthesis of α-Chiral Bicyclo[1.1.1]pentanes via Multicomponent Asymmetric Allylic Alkylation

被引：4

作者：

Barbeira-Aran, Sergio ^{[1
]}

Sanchez-Sordo, Irene ^{[1
]}

Fananas-Mastral, Martin ^{[1
]}

机构：

[1] Univ Santiago De Compostela, Ctr Singular Invest Quim Biolox & Mat Mol CiQUS, Santiago De Compostela 15782, Spain

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 18期

基金：

欧盟地平线“2020”; 欧洲研究理事会;

关键词：

CONJUGATE ADDITION; GRIGNARD-REAGENTS; DESIGN;

D O I：

10.1021/acs.orglett.4c00902

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bicyclo[1.1.1]pentanes (BCPs) have emerged as important structural motifs in drug design. However, asymmetric transformations that provide chiral BCPs bearing an adjacent stereocenter are still scarce. Here, we report a catalytic methodology for the enantioselective synthesis of alpha-chiral 1,3-difunctionalized BCPs from a three-component coupling of [1.1.1]propellane, a Grignard reagent, and an allylic phosphate. The reaction proceeds via the addition of the Grignard reagent to [1.1.1]propellane followed by an asymmetric N-heterocyclic carbene (NHC)-catalyzed allylic substitution of the resulting BCP-Grignard, providing a broad range of alpha-chiral BCPs with excellent levels of regioselectivity and enantioselectivity.

引用

页码：3784 / 3789

页数：6

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