Diastereoselective Construction of α‐Silyltetrahydropyranols through Silyl‐Oxa‐Prins Cyclization. Issue 4 (1st February 2017)

• Record Type: Journal Article
• Authors: Gandhamsetty, Narasimhulu; Jee, Soyeon; Chang, Sukbok
• Is Part Of: European journal of organic chemistry. Issue 4(2017)
• Page Start: 933
• Page End: 938
• Publication Date: 2017-02-01
• Subjects: Aldehydes -- Cyclization -- Diastereoselectivity -- Oxygen heterocycles -- Silicon; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601631
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : The Brønsted acid mediated selective silyl‐oxa‐Prins cyclization of α‐silyloxy homoallylsilanes with various aldehydes is achieved. Synthetically valuable α‐silyltetrahydropyranol products are obtained in high yields with excellent diastereoselectivities. Both syn ‐ and anti ‐isomeric tetrahydropyranols are selectively obtained by tuning the olefinic geometry of the substrates. Ms = methylsulfonyl.