Stereoselective synthesis of secondary and tertiary propargylic alcohols induced by a chiral sulfoxide auxiliary. Issue 2 (10th January 2019)

• Record Type: Journal Article
• Authors: Kobayashi, Daijiro; Miura, Motofumi; Toriyama, Masaharu; Motohashi, Shigeyasu
• Is Part Of: Tetrahedron letters. Volume 60:Issue 2(2019)
• Page Start: 120
• Page End: 123
• Publication Date: 2019-01-10
• Subjects: Alkynylation -- Chiral sulfoxide -- Diastereoselectivity -- Lithium acetylide; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.11.070
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: This method is possible to obtain a chiral propargylic alcohols which is important as a synthetic intermediate. Stereoselective alkynylation accomplished without additives. Aldehyde as well as ketone can be used as a substrate. Desulfurization was achieved with mild condition. Chiral propargylic alcohol with various substituents was synthesized. Abstract: The synthesis of optically active secondary and tertiary propargylic alcohols was accomplished by addition of lithium acetylide to chiral β-sulfinyl enones. Only a stoichiometric amount of the lithium acetylide was required and various substituents were tolerated. This reaction could be applied to substrates consisting of both ketones and aldehydes in high yields and excellent diastereoselectivities.