A general approach to the (S)- and (R)-isoflavans was invented, and efficiency of the method was demonstrated by the synthesis of (S)-equol ((S)-3), (R)-sativan ((R)-4), and (R)-vestitol ((R)-5). The key step is the allylic substitution of (S)-6a (Ar 1 =2,4-(MeO) 2 C 6 H 3 ) and (R)-6b (Ar 1 =2,4-(BnO) 2 C 6 H 3 ) with copper reagents derived from CuBr·Me 2 S and Ar 2 -MgBr (7a, Ar 2 =4-MeOC 6 H 4 ; 7b, 2,4-(MeO) 2 C 6 H 3 ; 7c, 2-MOMO-4-MeOC 6 H 3 ), furnishing anti S N 2′ products (R)-8a and (S)-8b,c with 93–97% chirality transfer in 60–75% yields. The olefinic part of the products was oxidatively cleaved and the Me and Bn groups on the Ar 1 moieties was then removed. Finally, phenol bromide 9a and phenol alcohols 9b,c underwent cyclization with K 2 CO 3 and the Mitsunobu reagent to afford (S)-3 and (R)-4 and -5, respectively.