Synthesis of a new 1,4-aminoalcohol and its use as catalyst in the enantioselective addition of organozinc to aldehydes

The synthesis of a new enantiopure, conformationally constrained 1,4-aminoalcohol is reported, starting from commercially available reagents from the chiral pool. This 1,4-aminoalcohol was used as chiral ligand in the addition of Et2Zn to aldehydes (best ee 98%) and in the synthesis of chiral propargylic alcohols (best ee 70%) by alkynylzinc species.

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(1S,5S,7R)-(3-Methyl-6,8-dioxa-3-aza-bicyclo[3.2.1]oct-7-yl)-methanolC7H13NO3Ee = 100%[α]D22=-91.2 (c 0.89, CHCl3)Source of chirality: (−)-2,3-O-isopropylidene-d-erythronolactoneAbsolute configuration: (1S,5S,7R)