Tetrahedron Letters

Tandem aldolization/lactonization/dyotropic rearrangement of α-amino-aldehydes

MT Reetz, A Schmitz, X Holdgrün

Index: Reetz, M.T.; Schmitz, A.; Holdgruen, X. Tetrahedron Letters, 1989 ,  vol. 30,  # 40  p. 5421 - 5424

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Citation Number: 30

Abstract

Abstract: N, N-Dibenzyl-protected a-amino-aldehydes 1 undergo non-chelationcontrolled aldol additions of 1-phenoxy-1-trimethylsiloxyethylene 2 followed by p-lactone formation and dyotropic rearrangement, all three reactions being catalyzed by MgClZ. The products, 4- substituted 3-amino-r-lactones 3, are stereochemically pure (de and ee> 99%).