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Diastereoselective Remote CH Activation by Hydroboration
Author(s) -
Varela Jesús A.,
Peña Diego,
Goldfuss Bernd,
Denisenko Dmitri,
Kulhanek Jiri,
Polborn Kurt,
Knochel Paul
Publication year - 2004
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.200400023
Subject(s) - hydroboration , stereoselectivity , stereocenter , chemistry , stereochemistry , bicyclic molecule , diol , aryl , ring (chemistry) , molecule , enantioselective synthesis , catalysis , organic chemistry , alkyl
Hydroboration of tetrasubstituted or trisubstituted alkenes with BH 3 and subsequent thermolysis allows remote diastereoselective CH activation of neighboring aryl rings. Tetrasubstituted and trisubstituted 1,1‐diphenylethylene derivatives undergo a highly stereoselective 1,2‐rearrangement followed by remote CH activation to lead, after oxidative workup, to a diol in which the relative stereochemistry of two stereocenters has been controlled. The mechanism of this remote activation has been studied and extended to related molecules that undergo this stereoselective CH activation, namely alkenylbiphenyl systems or alkenes with only one phenyl ring, such as alkenylbenzenes, or bicyclic systems. We have shown that this reaction allows diastereoselective synthesis of molecules with up to three contiguous chiral centers.