The first tandem inter-intramolecular catalytic asymmetric nitroaldol reaction utilizing a LnLi 3tris(( R)-binaphthoxide) complex (( R)-LnLB) (Ln: Lanthanoid)

Abstract

We have succeeded in synthesizing optically active (3aR,4R,5S,7aS)-3a,5-dihydroxy-7a-methyl-4-nitro-3a,4,5,6,7,7a-hexahydro-I-indanone ( 3b) with 65% ee in one-pot from aldehyde 1 and nitromethane using a tandem inter-intramolecular catalytic asymmetric nitroaldol reaction promoted by LnLi 3tris((R)-binaphthoxide) (LnLB; Ln = lanthanoid) and after crystallization 3b with 79% ee was isolated in 41% yield. In addition, after recrystallization, the optical purity of 3b was increased to 96% ee.