Catalytic Asymmetric Synthesis of Butenolides and Butyrolactones
Author(s) -
Bin Mao,
Martín FañanásMastral,
Ben L. Feringa
Publication year - 2017
Publication title -
chemical reviews
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 20.528
H-Index - 700
eISSN - 1520-6890
pISSN - 0009-2665
DOI - 10.1021/acs.chemrev.7b00151
Subject(s) - chemistry , butenolide , enantioselective synthesis , optically active , combinatorial chemistry , total synthesis , catalysis , nanotechnology , stereochemistry , biochemical engineering , organic chemistry , materials science , engineering
γ-Butenolides, γ-butyrolactones, and derivatives, especially in enantiomerically pure form, constitute the structural core of numerous natural products which display an impressive range of biological activities which are important for the development of novel physiological and therapeutic agents. Furthermore, optically active γ-butenolides and γ-butyrolactones serve also as a prominent class of chiral building blocks for the synthesis of diverse biological active compounds and complex molecules. Taking into account the varying biological activity profiles and wide-ranging structural diversity of the optically active γ-butenolide or γ-butyrolactone structure, the development of asymmetric synthetic strategies for assembling such challenging scaffolds has attracted major attention from synthetic chemists in the past decade. This review offers an overview of the different enantioselective synthesis of γ-butenolides and γ-butyrolactones which employ catalytic amounts of metal complexes or organocatalysts, with emphasis focused on the mechanistic issues that account for the observed stereocontrol of the representative reactions, as well as practical applications and synthetic potentials.
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