Doubly Stereoconvergent Propargylic Alkylation of α-Cyanocarbonyls: Enantioselective Construction of Vicinal Stereocenters

被引：0
作者：
Ghosh, Suman [1 ]
Mukherjee, Santanu [1 ]
机构：
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, India
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 36期
关键词：
QUATERNARY STEREOCENTERS; SYNERGISTIC CATALYSIS; ADJACENT QUATERNARY; ALLYLIC ALKYLATION; TERTIARY; ANNULATION; DIASTEREO; CASCADE; PYBOX;
D O I：
10.1021/acs.orglett.4c02880
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An asymmetric propargylic alkylation of alpha-cyanocarbonyls is developed for the first time under cooperative Cu(I) and organocatalysis. With ethynyl benzoxazinanones as the propargylic electrophile, this decarboxylative doubly stereoconvergent reaction evades alkyne hydroamination to furnish acyclic alpha-propargylic cyanocarbonyls, bearing vicinal tertiary and quaternary stereocenters, with high diastereo- and enantioselectivity (up to >20:1 dr and 99.5:0.5 er).
引用
收藏
页码：7733 / 7738
页数：6
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