Catalytic Enantioselective Synthesis of Trisubstituted Secondary Allylic Alcohols Starting from Terminal Alkynes and Aldehydes. Issue 33 (22nd October 2015)

• Record Type: Journal Article
• Authors: Morimoto, Haruki; Harada, Toshiro
• Is Part Of: European journal of organic chemistry. Issue 33(2015)
• Page Start: 7378
• Page End: 7383
• Publication Date: 2015-10-22
• Subjects: Asymmetric catalysis -- Asymmetric synthesis -- Nucleophilic addition -- Allylic compounds -- Aluminium -- ­Titanium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500910
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A general one‐pot method for the enantioselective synthesis of β, β‐disubstituted allylic alcohols has been developed starting from readily available terminal alkynes and aldehydes. Trisubstituted ( E )‐vinylaluminium reagents, generated regio‐ and stereoselectively by the Zr‐catalyzed carboalumination of the alkynes with Me3 Al, was used in subsequent enantioselective addition reactions with aldehydes using a DPP‐H8 ‐BINOL‐derived titanium catalyst system at low catalyst loading (5 mol‐%). Abstract : A general one‐pot method for the enantioselective synthesis of β, β‐disubstituted allylic alcohols has been developed starting from terminal alkynes and aldehydes. Trisubstituted vinylaluminium reagents, generated by a Zr‐catalyzed carboalumination, can be used successfully in subsequent enantioselective addition reactions with aldehydes using a DPP‐H8 ‐BINOL‐derived titanium catalyst (5 mol‐%).