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Asymmetric aldol reactions of chiral Ni(II)-complex of glycine with aliphatic aldehydes. Stereodivergent synthesis of syn-(2S)- and syn-(2R)-β-alkylserines

✍ Scribed by Vadim A Soloshonok; Dimitry V Avilov; Valery P Kukhar'; Vitali I Tararov; Tatiana F Savel'eva; Tatiana D Churkina; Nicolai S Ikonnikov; Konstantin A Kochetkov; Svetlana A Orlova; Alexander P Pysarevsky; Yuri T Struchkov; Nikolai I Raevsky; Yuri N Belokon'

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
976 KB
Volume
6
Category
Article
ISSN
0957-4166

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✦ Synopsis

Stereoselectivity of aldol reactions between aliphatic aldehydes and Ni(ll)-complex of chiral non-racemic Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone (BPB) in the presence of excess of MeONa, has been studied as a function of time, reaction conditions and nature of an aldehyde. Two salient features of the reaction, very high pseudokinetic syn-(2S)-diastereoselectivity, and dependence of thermodynamic syn~2R)-diastereoselectivity on the steric bulk of an aldehyde side chain, were disclosed and used for efficient (more than 90% de and ee) asymmetric synthesis of both syn-(2S) and syn-(2R)-3-alkyl substituted serines. Synthetic potential and reliability of this asymmetric method are demonstrated with the large scale (2-20 g) preparation of enantiomerically pure amino acids.

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Direct enantioselective synthesis of syn
Direct enantioselective synthesis of syn-1,3-diols by the reaction of aldehydes with enol silyl ethers in the presence of a chiral borane complex. Successive asymmetric aldol reaction and asymmetric reduction with one promoter
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## A stoicbiometric Itmomtofthccbiral~1turntdouttos tlaxssivcly promote the aqmmehic aldol rcactioa of al&hy&s with cd silyl ethers and the rdowitlg asymmettic leductioa in om pot to affcrd syI&l3diols willlbighetity.

ChemInform Abstract: Highly Diastereosel
ChemInform Abstract: Highly Diastereoselective Aza-Aldol Reactions of a Chiral Ni(II) Complex of Glycine with Imines. An Efficient Asymmetric Approach to 3- Perfluoroalkyl-2,3-diamino Acids.
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## 1997 aminocarboxylic acids aminocarboxylic acids (hydrazinocarboxylic acids) and esters (acyclic compounds) P 0270 ## 40 -103 Highly Diastereoselective Aza-Aldol Reactions of a Chiral Ni(II) Complex of Glycine with Imines. An Efficient Asymmetric Approach to 3-Perfluoroalkyl-2,3-diamino Acids.