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Diastereoselective Construction of α‐Silyltetrahydropyranols through Silyl‐Oxa‐Prins Cyclization
Author(s) -
Gandhamsetty Narasimhulu,
Jee Soyeon,
Chang Sukbok
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601631
Subject(s) - chemistry , prins reaction , silylation , stereochemistry , organic chemistry , catalysis
The Brønsted acid mediated selective silyl‐oxa‐Prins cyclization of α‐silyloxy homoallylsilanes with various aldehydes was achieved. Synthetically valuable α‐silyltetrahydropyranol products were obtained in high yields with excellent diastereoselectivities. Both syn ‐ and anti ‐isomeric tetrahydropyranols were selectively obtained by tuning the olefinic geometry of the substrates. The procedure is operationally simple and convenient to perform even on a large scale under mild conditions.