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Non‐Chelate‐Controlled Addition of 1‐Bromo‐1‐lithio‐1‐alkenes to O ‐Protected Lactaldehydes
Author(s) -
Braun Manfred,
Mahler Hellmut
Publication year - 1989
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.198908961
Subject(s) - alkene , chelation , halogenation , formal synthesis , carbenoid , chemistry , ozonolysis , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , rhodium
Non‐chelate control is generally difficult to realize. With the carbenoid 2 it has now been possible for the first time to carry out such an addition (85 % de ) of an organolithium compound to the protected lactaldehyde ( S )‐ 1 . A chiral 1 bromo‐l‐lithio‐l‐alkene increases the diastereoselectivity to 95 % de . The product 4 separated the formal after dehalogenation and ozonolysis is formed by the formal addition of ⊖CH 2 OH.