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Unprecedented Facial Diastereoselectivity in the Paternò–Büchi Reaction of a Chiral Dihydropyrrole—A Short Total Synthesis of (+)‐Preussin
Author(s) -
Bach Thorsten,
Brummerhop Harm
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981231)37:24<3400::aid-anie3400>3.0.co;2-3
Subject(s) - oxetane , chemistry , stereochemistry , organic chemistry
An apparently unexpected, but gratifying facial diasteroselecitvity was observed in the Paternò–Büchi reaction of the chiral dihydropyrrole 1 . The oxetane 2 was formed as the major product of the syn ‐selective photocycloaddition and can be transformed to the pyrrolidinol alkaloid (+)‐preussin ( 3 ) in two steps.