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Highly Diastereoselective Synthesis and Epoxidation of Chiral 1,2‐Dihydronaphthalenes
Author(s) -
Linker Torsten,
Peters Karl,
Peters EvaMaria,
Rebien Frank
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199624871
Subject(s) - stereocenter , phenyllithium , oxazoline , chemistry , yield (engineering) , nucleophile , chiral auxiliary , stereoselectivity , nucleophilic addition , stereochemistry , enantioselective synthesis , organic chemistry , catalysis , materials science , metallurgy
Four stereogenic centers are generated with high diastereoselectivity in only a few steps starting from 2‐naphthoic acid ( 1 ). Meyers oxazoline synthesis, nucleophilic addition of phenyllithium, and epoxidation afford rac ‐ 2 in 63% overall yield. The stereochemical course of the reaction is directed by the phenyl group.