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- Title
Stereodivergent Synthesis of Functionalized Tetrahydropyrans Accelerated by Mechanism-Based Allylboration and Bioinspired Oxa-Michael Cyclization.
- Authors
Yang, Lin; Lin, Zuming; Huang, Sha ‐ Hua; Hong, Ran
- Abstract
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.
- Subjects
TETRAHYDROPYRANYL compounds synthesis; HETEROCYCLIC compounds synthesis; CYCLIC compounds synthesis; ALLYLBORATION; ORGANIC synthesis research
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 21, p6388
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201600558