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Stereoselective Synthesis of anti ‐1,4‐Diols by a BH 3 ⋅THF‐Mediated Rearrangement of 1,2‐Disubstituted Cyclobutenes
Author(s) -
Knapp Kolja M.,
Goldfuss Bernd,
Knochel Paul
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200304902
Subject(s) - stereoselectivity , stereochemistry , chemistry , organic chemistry , catalysis
A new stereoselective rearrangement of cyclobutylboranes, obtained by the hydroboration of 1,2‐disubstituted cyclobutenes, provides anti ‐1,4‐diols with good‐to‐excellent diastereoselectivity. The mechanism of the rearrangement is discussed based on theoretical calculations.