Base‐Promoted C→N Acyl Rearrangement: An Unconventional Approach to α‐Amino Acid Derivatives | Zendy

Ugarriza Iratxe | Zendy; Uria Uxue | Zendy; Carrillo Luisa | Zendy; Vicario Jose L. | Zendy; Reyes Efraim | Zendy

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Base‐Promoted C→N Acyl Rearrangement: An Unconventional Approach to α‐Amino Acid Derivatives

Author(s) -

Ugarriza Iratxe,

Uria Uxue,

Carrillo Luisa,

Vicario Jose L.,

Reyes Efraim

Publication year - 2014

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201402514

Subject(s) - chemistry , alkyl , alkylation , nucleophile , intramolecular force , yield (engineering) , carroll rearrangement , tandem , cope rearrangement , rearrangement reaction , stereochemistry , base (topology) , medicinal chemistry , sigmatropic reaction , combinatorial chemistry , organic chemistry , catalysis , physics , mathematics , composite material , mathematical analysis , materials science , thermodynamics

We have discovered that N ‐alkyl aminomalonates undergo a fast and selective intramolecular C→N acyl rearrangement reaction in the presence of a strong base, leading to N ‐protected glycinates in excellent yield. Moreover, the fact that the reaction proceeds through a nucleophilic enolate intermediate has been used for implementing a tandem rearrangement/alkylation sequence that has been applied to the preparation of synthetically relevant nonproteinogenic tertiary and quaternary N ‐alkyl α‐amino acids in a very simple and reliable way.

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