Gold-catalyzed [4+3] and [4+4]-annulation reactions of t-butyl propiolate derivatives with epoxides and oxetanes for the construction of 1, 4-dioxepane and 1, 5-dioxocane cores. Issue 47 (20th May 2016)

• Record Type: Journal Article
• Authors: Sahani, Rajkumar Lalji; Liu, Rai-Shung
• Is Part Of: Chemical communications. Volume 52:Issue 47(2016)
• Page Start: 7482
• Page End: 7485
• Publication Date: 2016-05-20
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc02124g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Gold-catalyzed [4+ n ]-annulations ( n = 3, 4) of tert -butyl propiolate derivatives with epoxides or oxetanes proceed smoothly to yield seven- or eight-membered oxacyclic products efficiently. Abstract : Gold-catalyzed [4+ n ]-annulations ( n = 3, 4) of tert -butyl propiolate derivatives with epoxides or oxetanes proceed smoothly to yield seven- or eight-membered oxacyclic products efficiently. In the context of the [4+3]-annulations, product analysis reveals a retention of stereochemistry upon the intramolecular SN 2 attack of an epoxide. We also report the [4+5]-annulation between one tert -butyl propiolate and γ-lactol, to manifest the utility toward medium-sized rings.