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Stereodivergent Synthesis of Functionalized Tetrahydropyrans Accelerated by Mechanism‐Based Allylboration and Bioinspired Oxa‐Michael Cyclization
Author(s) -
Yang Lin,
Lin Zuming,
Huang ShaHua,
Hong Ran
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600558
Subject(s) - hydroboration , allene , chemistry , borane , michael reaction , aldehyde , stereoselectivity , reagent , combinatorial chemistry , organic chemistry , catalysis
A stereodivergent strategy enabled by bioinspired oxa‐Michael cyclization was developed for the synthesis of functionalized tetrahydropyrans on the basis of the inherent symmetry in 1,3‐diols, the symmetries of which were tunable by stereoselective hydroboration of an allene with a variety of alkylborane reagents and subsequent allylation of an aldehyde. The mechanism‐based utilization of monoalkyl borane in the hydroboration and allylation cascade is unprecedented.