T. Sano et T. Oriyama, Development of catalytic asymmetric acylation of alcohols in the presence of a chiral 1,2-diamine, J SYN ORG J, 57(7), 1999, pp. 598-607
Asymmetric acylation of alcohols is very important in synthetic organic che
mistry and holds great potential for the preparation of small chiral compou
nds which are suited for further manipulation in the synthesis of biologica
lly active natural products. Although enzymatic acylation has been extensiv
ely studied and established as a promising method for the preparation of ch
iral alcohol variants, development of nonenzymatic alternatives in this fie
ld has been scattered. From this viewpoint, Re wish to demonstrate highly e
fficient and practical methods for the catalytic asymmetric acylation of ra
cemic secondary alcohols and various meso-diols by the reaction with achira
l benzoyl chloride in the presence of a chiral 1,2-diamine derived from (S)
-proline.