Diastereoselective Construction of α‐Silyltetrahydropyranols through Silyl‐Oxa‐Prins Cyclization | Zendy

Gandhamsetty Narasimhulu | Zendy; Jee Soyeon | Zendy; Chang Sukbok | Zendy

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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.

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