A Straightforward Sequential Approach for the Enantioselective Synthesis of Optically Active α‐Arylmethanol‐1, 2, 3‐Triazoles. Issue 40 (20th August 2018)

• Record Type: Journal Article
• Authors: Andrade, Floyd C. D.; Pugnal, Lucas V. B. L.; Betim, Hugo L. I.; Vani, Jéssica F.; Zukerman‐Schpector, Julio; Schwab, Ricardo S.
• Is Part Of: European journal of organic chemistry. Issue 40(2018)
• Page Start: 5467
• Page End: 5476
• Publication Date: 2018-08-20
• Subjects: Di(hetero)arylmethanols -- 1, 2, 3‐triazoles -- Propargylic alcohols -- Enantioselective alkynylation -- 1, 3‐dipolar cycloaddition; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800751
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : Herein we describe a compelling sequential methodology for obtaining optically active α‐arylmethanols‐1, 2, 3‐triazoles. The approach is based on the enantioselective alkynylation of aldehydes followed by a one‐pot two‐step desilylation/Cu I ‐catalyzed azide‐alkyne 1, 3‐dipolar cycloaddition (CuAAC), providing the corresponding products with excellent yields and high levels of enantioselectivity. Furthermore, the click chemistry can be performed without affecting the enantiomeric excess. The application of the reaction has been demonstrated in the synthesis of a 1, 2, 3‐triazole analog of antihistaminic and anticholinergic drug ( R )‐orphenadrine. Abstract : Click here! Chiral arylmethanols bearing 1, 2, 3‐triazoles are achieved using a sequential approach based on the enantioselective alkynylation of aldehydes followed by a one‐pot two‐step desilylation/CuAAC, providing the corresponding products with excellent yields and high enantioselectivity. The application of the reaction has been demonstrated in the synthesis of a 1, 2, 3‐triazole analog of antihistaminic and anticholinergic drug ( R )‐orphenadrine.