Highly diastereoselective synthesis of the 1,1'-binaphthol unit on a bile acid template
The use of 7-deoxycholic acid as a chiral template in the asymmetric syntheses of 1,1'-binaphthyl-2,2'-diol derivatives is reported. Intramolecular coupling of compounds 7 and 11 have been carried out with Mn(acac)(3) in CH(3)CN to afford coupled binaphthol products 8 and 12 with 65% and >99% diastereoselectivity, respectively. In both cases the predominant formation of the (S) isomers were predicted by computer modeling studies. This was confirmed in the case of compound 12.
Bandyopadhyaya
AK
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
Sangeetha
NM
Maitra
U