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Reactivity of α‐Bromosulfones Obtained from gem ‐Dibromides
Author(s) -
Münster Niels,
Werel Laura,
Rennar Georg Alexander,
Harms Klaus,
Koert Ulrich
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501136
Subject(s) - chemistry , steric effects , stereoselectivity , reactivity (psychology) , bromine , medicinal chemistry , chelation , substitution reaction , stereochemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
α‐Bromosulfones have been synthesized diastereoselectively by reaction of β‐hydroxy gem ‐dibromides with aromatic sulfinates. More steric demanding groups in the β‐position led to increased stereoselectivity in these S N 2 reactions. Lithiated α‐bromosulfones react diastereoselectively with alkylating agents, aldehydes, and ketones. No configurational stability of the lithiated α‐bromosulfones was observed except fast equilibration towards a chelate‐stabilized intermediate. Treatment of the α‐bromosulfone with methylcuprate resulted in substitution of the bromine by a methyl group.