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Novel Route to (+)‐Pinitol Intermediate via a Strategy Derived from Diazotization of O ‐Isopropylidene‐Protected 4‐Amino‐2‐Cyclohexen‐1‐ol
Author(s) -
Lin KuoWei,
Wang YingChuan,
Yan TuHsin
Publication year - 2008
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200800062
Subject(s) - chemistry , enantiopure drug , epoxide , epoxy , cyclohexene , block (permutation group theory) , organic chemistry , cycloaddition , alcohol , stereochemistry , combinatorial chemistry , enantioselective synthesis , catalysis , combinatorics , mathematics
A concise preparation of the enantiopure 1,2‐(isopropylidenedioxy)‐3,4‐epoxy‐5‐cyclohexene 2b , which is an important building block for (+)‐pinitol synthesis, evolved by combining the asymmetric cycloaddition of isopropylidenedioxy)cyclohexadiene to chiral chloronitroso with an internal substitution of an amino alcohol to create vinyl epoxide.