Asymmetric tandem Wittig rearrangement/Mannich reactions.
Journal: Angewandte Chemie (International Ed. In English)
Published:
Abstract
The choice is yours: a highly stereoselective synthesis of α-alkyl-α-hydroxy-β-amino esters is accomplished through a tandem Wittig-rearrangement/Mannich reaction sequence. Transformations of N-benzyl or N-Boc imines proceed with high selectivity for formation of syn-amino alcohol derivatives, whereas N-Boc-2-(phenylsulfonyl)amines generate anti-amino alcohol products. Auxiliary cleavage (transesterification or reduction) yields enantiomerically enriched products with up to 96 % ee.
Authors
Natalie Giampietro, John Wolfe