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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 .