Asymmetric tandem Wittig rearrangement/Mannich reactions.
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.
Department of Chemistry, University of Michigan, Ann Arbor, 48109-1055, USA.
Natalie C
NC
Giampietro
John P
JP
Wolfe
D000605:Amino Alcohols / Q000138:chemical synthesis*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000605:Amino Alcohols; D007097:Imines