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. 2009 Jul 15;131(27):9473-4.
doi: 10.1021/ja902591g.

Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: a new catalytic route to beta3-amino acids

Barbara Weiner  1 , Alejandro Baeza, Thomas Jerphagnon, Ben L Feringa
Affiliations

Aldehyde selective Wacker oxidations of phthalimide protected allylic amines: a new catalytic route to beta3-amino acids

Barbara Weiner et al. J Am Chem Soc. .

Abstract

A new method for the synthesis of beta(3)-amino acids is presented. Phthalimide protected allylic amines are oxidized under Wacker conditions selectively to aldehydes using PdCl(2) and CuCl or Pd(MeCN)(2)Cl(NO(2)) and CuCl(2) as complementary catalyst systems. The aldehydes are produced in excellent yields and exhibit a large substrate scope. Beta-amino acids and alcohols are synthesized by oxidation or reduction and subsequent deprotection.

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