Phosphine‐Catalyzed Synthesis of Chiral N‐Heterocycles through (Asymmetric) P(III)/P(V) Redox Cycling. Issue 22 (15th June 2021)

• Record Type: Journal Article
• Authors: Lorton, Charlotte; Saleh, Nidal; Voituriez, Arnaud
• Is Part Of: European journal of organic chemistry. Issue 22(2021)
• Page Start: 3340
• Page End: 3344
• Publication Date: 2021-06-15
• Subjects: Asymmetric synthesis -- Dihydro-1H-pyrrole -- Organocatalysis -- Phosphine -- Tetrahydropyridine; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202100404
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Phosphine‐catalyzed tandem Michael addition/intramolecular Wittig reactions have been developed for the synthesis of chiral 2, 5‐dihydro‐1 H ‐pyrrole and tetrahydropyridine derivatives. These processes have been rendered catalytic in phosphine, thanks to the in situ reduction of phosphine oxide by phenylsilane. Furthermore, catalytic and asymmetric P(III)/P(V) processes were implemented using enantiopure chiral phosphines. Abstract : An access to chiral 2, 5‐dihydro‐1 H ‐pyrroles and tetrahydropyridines has been elaborated through a phosphine‐catalyzed Michael addition/Wittig reaction. The use of catalytic amounts of chiral phosphines affords these nitrogen heterocycles with promising enantioselectivities.