Chiral Inductive Diastereoconvergent Allylation Reactions of Allyltrimethylsilane and Diastereomixtures of Diarylmethanols Catalyzed by FeCl3. Issue 46 (30th October 2018)

• Record Type: Journal Article
• Authors: Fujihara, Rina; Nakata, Kenya
• Is Part Of: European journal of organic chemistry. Issue 46(2018)
• Page Start: 6566
• Page End: 6573
• Publication Date: 2018-10-30
• Subjects: Allylation -- Chiral auxiliaries -- Carbocations -- Diastereoselectivity -- Tolterodine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801236
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : We report the chiral‐auxiliary‐controlled diastereoconvergent allylation reactions of allyltrimethylsilane with diastereomeric mixtures of diarylmethanols in the presence of FeCl3 as a Lewis acid catalyst. This reaction was successfully applied to a variety of substrates; it proceeded irrespective of the substituent on the aromatic ring of the substrate. The present method was used as the key step in synthesizing ( R )‐tolterodine. Abstract : Diastereoconvergent Manner: FeCl3 ‐catalyzed chiral‐auxiliary‐controlled diastereoconvergent allylation reactions of allyltrimethylsilane with diastereomeric mixtures of diarylmethanols were achieved with high yields and selectivities.