Tetrahedron letters

Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids. Applications in Wittig reactions and heterocycle synthesis

SB Davies, MA McKervey

Index: Davies, Simon B.; McKervey, M. Anthony Tetrahedron Letters, 1999 , vol. 40, # 6 p. 1229 - 1232

Full Text: HTML

Citation Number: 50

Abstract

NZ-γ-amino alcohols derived from nonracemic β-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniie,(S)-(−)-coniceine and a pipecoline precursor is described.

Related Articles:

Camphor-based α-bromo ketones for the asymmetric Darzens reaction

[Palomo, Claudio; Oiarbide, Mikel; Gonzalez-Rego, M. Concepcion; Sharma, Arun K.; Garcia, Jesus M.; Gonzalez, Alberto; Landa, Cristina; Linden, Anthony Angewandte Chemie - International Edition, 2000 , vol. 39, # 6 p. 1063 - 1066]

Exceptionally Simple Homologation of Protected α??to β??Amino Acids in the Presence of Silica Gel

[Koch, Karen; Podlech, Joachim Synthetic Communications, 2005 , vol. 35, # 21 p. 2789 - 2794]

Camphor-based α-bromo ketones for the asymmetric Darzens reaction

[Palomo, Claudio; Oiarbide, Mikel; Gonzalez-Rego, M. Concepcion; Sharma, Arun K.; Garcia, Jesus M.; Gonzalez, Alberto; Landa, Cristina; Linden, Anthony Angewandte Chemie - International Edition, 2000 , vol. 39, # 6 p. 1063 - 1066]

Chemoenzymatic synthesis of 4-amino-2-hydroxy acids: a comparison of mutant and wild-type oxidoreductases

[Sutherland, Andrew; Willis, Christine L. Journal of Organic Chemistry, 1998 , vol. 63, # 22 p. 7764 - 7769]

Chemoenzymatic synthesis of 4-amino-2-hydroxy acids: a comparison of mutant and wild-type oxidoreductases

[Sutherland, Andrew; Willis, Christine L. Journal of Organic Chemistry, 1998 , vol. 63, # 22 p. 7764 - 7769]

More Articles...