title: Stereodivergent Synthesis of Functionalized Tetrahydropyrans Accelerated by Mechanism-Based Allylboration and Bioinspired Oxa-Michael Cyclization.
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.
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry (CAS), 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Lin
authors.initials: L
authors.lastname: Yang
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry (CAS), 345 Lingling Road, Shanghai, 200032, China.
authors.forename: Zuming
authors.initials: Z
authors.lastname: Lin
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry (CAS), 345 Lingling Road, Shanghai, 200032, China. shahua@sit.edu.cn.|School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, China. shahua@sit.edu.cn.
authors.forename: Sha-Hua
authors.initials: SH
authors.lastname: Huang
authors.affiliation: CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry (CAS), 345 Lingling Road, Shanghai, 200032, China. rhong@sioc.ac.cn.
authors.forename: Ran
authors.initials: R
authors.lastname: Hong
keywords: Michael addition; allenes; boranes; heterocycles; homoallylic alcohols