Methods for Synthesis of Chiral Alcohols and Their Conversion to Heterocycles Containing Bi‐2‐Naphthyl Moiety. Issue 3 (20th January 2020)

• Record Type: Journal Article
• Authors: Periasamy, Mariappan; Venkanna, Boda; Mohan, Lakavathu
• Is Part Of: ChemistrySelect. Volume 5:Issue 3(2020)
• Page Start: 1088
• Page End: 1091
• Publication Date: 2020-01-20
• Subjects: Acylation -- Amination -- bi-2-naphthol -- cyclization -- N-heterocycles -- oxazaborolidine -- reduction.; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201903644
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Convenient methods were developed for the preparation of chiral alcohols containing bi‐2‐naphthyl moiety in 92–96% yields. The substituted 1, 4‐diols containing bi‐2‐naphthyl moiety were further converted to N ‐substituted pyrrolidine derivatives in 72%‐76% yields via the corresponding dimesylate followed by reaction with primary amines. Interestingly, the corresponding chiral tetrahydrofuran derivative was obtained in 90% yield by self condensation of the dimesylate in the absence of primary amines. The results are discussed considering the reaction mechanisms involved in these transformations. Abstract : Convenient methods have been developed for the preparation of chiral alcohols containing bi‐2‐naphthyl moiety in 92–96% yields. Also, the substituted BINOL derivatives have been further converted to the chiral 2‐substituted tetrahydrofuran and N‐substituted pyrrolidine in 72–90% yields. The cyclised products were obtained selectively via elimination of mesityl chloride.