In:
European Journal of Organic Chemistry, Wiley, Vol. 2009, No. 5 ( 2009-02), p. 716-720
Abstract:
The pinacol coupling reaction of ( Rp )‐2‐diphenylphosphanyl ferrocenecarbaldehyde ( 1 ) was smoothly mediated by divalent samarium triflate to give ( R , R )‐diol 2a predominantly, whereas the use of samarium(II) iodide resulted in low selectivity as described in the previous literature. In contrast, the coupling reaction of ( Rp )‐2‐diphenylphosphoryl ferrocenecarbaldehyde ( 3 ) with Sm(OTf) 2 gave the ( S , S )‐diol as the major isomer, which was the opposite stereochemistry of that obtained in the reaction with 1 . The rhodium complexes of diphosphanes 2a were good catalysts for the asymmetric hydrogenation of α‐acetamidocinnamic acid, and the product was obtained quantitatively with up to 92 % ee . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Type of Medium:
Online Resource
ISSN:
1434-193X
,
1099-0690
DOI:
10.1002/ejoc.v2009:5
DOI:
10.1002/ejoc.200801138
Language:
English
Publisher:
Wiley
Publication Date:
2009
detail.hit.zdb_id:
1475010-7
Bookmarklink