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Synthesis of Racemic and Enantiomerically Pure ( R*,R*,R* )‐Tris(α‐methylbenzyl)phosphane − X‐ray Crystal Structures of the Phosphane Oxides and Borane Complexes
Author(s) -
Wyatt Paul,
Eley Helen,
Charmant Jonathan,
Daniel Berian J.,
Kantacha Anob
Publication year - 2003
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.200300396
Subject(s) - chemistry , electrophile , iodide , borane , nucleophile , enantioselective synthesis , reagent , tris , stereochemistry , medicinal chemistry , organic chemistry , catalysis , biochemistry
An asymmetric synthesis of C 3 ‐symmetric phosphane 1 has been achieved. Two of the α‐methylbenzyl groups were introduced as nucleophiles (using an α‐methylbenzyl Grignard reagent), and asymmetry was introduced by resolution using ( R )‐α‐methylbenzylamine. The final α‐methylbenzyl group was introduced as an electrophile (α‐methylbenzyl iodide) in a modestly selective reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)