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Synthesis and Crystal Structure of a Chiral C 3 ‐Symmetric Monophosphane
Author(s) -
Bolm Carsten,
Davis William M.,
Halterman Ronald L.,
Sharpless K. Barry
Publication year - 1988
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198808351
Subject(s) - stereocenter , enantiomer , bromide , chemistry , atom (system on chip) , transition metal , optically active , crystallography , crystal structure , nuclear magnetic resonance spectroscopy , spectroscopy , stereochemistry , metal , resolution (logic) , enantioselective synthesis , catalysis , organic chemistry , physics , quantum mechanics , artificial intelligence , computer science , embedded system
The C 3 ‐symmetric compounds 1 (R = H, t Bu) are chiral phosphanes without a stereogenic C atom. A mutarotational energy of 11.8 kcal mol ‐1 was determined for the benzylphosphonium bromide of 1 , R = H, by 1 H‐NMR spectroscopy. Resolution of the enantiomers was not achieved. Optically active C 3 ‐symmetric phosphane ligands are expected to exhibit good chiralitytransfer properties in transition‐metal‐catalyzed reactions.