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Journal Article

ASYMMETRIC AZA DIELS-ALDER REACTIONS OF AMINO-ACID ESTER IMINES WITH BRASSARD-DIENE

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Waldmann, H., BRAUN, M., & DRAGER, M. (1991). ASYMMETRIC AZA DIELS-ALDER REACTIONS OF AMINO-ACID ESTER IMINES WITH BRASSARD-DIENE. TETRAHEDRON-ASYMMETRY, 2(12), 1231-1246. doi:10.1016/S0957-4166(00)80023-3.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-9AD7-0
Abstract
Imines 1 obtained from aromatic, aliphatic or functionalized aldehydes and valine tert-butyl ester undergo Lewis acid catalyzed hetero Diels-Alder reactions with Brassard's diene 2. The cycloadducts are formed in good to high yields and with diastereomer ratios of 92:8-97:3. For the removal of the chiral auxiliary group a new method was developed whose principle consists in the conversion of the amino acid alpha-C-atom into an acetalic center employing a Curtius rearrangement as the key step.