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Stereoselective Synthesis of Alcohols, XXXVII. Origins of Stereoselectivity in Reactions of α‐Substituted Allylboronates with Aldehydes
Author(s) -
Hoffmann Reinhard W.,
Jens Wolff J.
Publication year - 1991
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19911240323
Subject(s) - chemistry , stereoselectivity , context (archaeology) , aldehyde , stereochemistry , medicinal chemistry , organic chemistry , catalysis , paleontology , biology
Rate constants for the addition of α‐substituted allylboronates 4 (XH, Cl, Br, OCH 3 , SCH 3 ] to aldehydes have been measured. The results have been used to differentiate between different models that have been advanced to account for the high proportion of (Z)‐configurated homoallyl alcohols 5 formed in allylboration reactions. Attempts have been made in this context to detect ate‐complex formation between benzylboronates and aldehydes.