Rhodium-Catalyzed Asymmetric Conjugate Alkynylation/Aldol Cyclization Cascade for the Formation of α-Propargyl-β-hydroxyketones

被引：22

作者：

Choo, Ken-Loon ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 05期

基金：

加拿大自然科学与工程研究理事会;

关键词：

TANDEM 1,4-ADDITION-ALDOL REACTION; REDUCTIVE ALDOL REACTION; ENANTIOSELECTIVE SYNTHESIS; ARYLATIVE CYCLIZATION; ORGANOBORON REAGENTS; ORGANOZINC REAGENTS; PHOSPHINE-LIGANDS; CYCLIC ENONES; KETONES; HYDROALKYNYLATION;

D O I：

10.1021/acs.orglett.8b00153

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium-catalyzed conjugate alkynylation/aldol cyclization cascade was developed. Densely function-alized cyclic alpha-propargyl-beta-hydroxyketones were synthesized with simultaneous formation of a C(sp)-C(sp(3)) bond, a C(sp(3))-C(sp(3)) bond, as well as three new contiguous stereocenters. The transformation was achieved with excellent enantio-and diastereoselectivities using BINAP as the ligand. The synthetic utility of the newly installed alkynyl moiety was exhibited by subjecting the products to an array of derivatizations.

引用

页码：1380 / 1383

页数：4

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