Chirale Induktion bei photochemischen Reaktionen, VI. Asymmetrische Steuerung der Addition von Semipinakol‐radikalen an chirale Malein‐ und Fumarsäureester | Zendy

Vaßen Reiner | Zendy; Runsink Jan | Zendy; Scharf HansDieter | Zendy

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Chirale Induktion bei photochemischen Reaktionen, VI. Asymmetrische Steuerung der Addition von Semipinakol‐radikalen an chirale Malein‐ und Fumarsäureester

Author(s) -

Vaßen Reiner,

Runsink Jan,

Scharf HansDieter

Publication year - 1986

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19861191125

Subject(s) - chemistry , diastereomer , fumaric acid , maleic acid , medicinal chemistry , maleic anhydride , radical , stereochemistry , organic chemistry , copolymer , polymer

Chiral Induction in Photochemical Reactions, VI. — Asymmetric Control of the Addition of Hemipinacol Radicals to Chiral Maleates and Fumarates The photocatalysed addition of 2‐propanol ( 2 ) to the monoesters of maleic acid 1b and 1d yields the esters of terebic acid 5b und 5d with a diastereoselectivity up to 62% de. The major diastereomer 5d has (2 S )‐configuration. Diastereoselectivity of 23% maximum are observed by applying the (−)‐menthyl diesters of maleic or fumaric acid 1c and 1e . The product obtained is the acyclic diaterebic acid ester 4c .

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