Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl l-alanine amide-derived ammonium ylides-Reference-Cited by-同舟云学术

Double axial chirality promoted asymmetric [2,3] Stevens rearrangement of N-cinnamyl l-alanine amide-derived ammonium ylides

Published:2014 Issue:52 Volume:50 Page:6860-6862
ISSN:1359-7345
Container-title:Chem. Commun.
language:en
Short-container-title:Chem. Commun.

Author:

Tayama Eiji¹²³⁴,Naganuma Noriko¹²³⁴,Iwamoto Hajime¹²³⁴,Hasegawa Eietsu¹²³⁴

Affiliation:

1. Department of Chemistry

2. Faculty of Science

3. Niigata University

4. Niigata, Japan

Abstract

The base-induced asymmetric [2,3] Stevens rearrangement of N-cinnamyl tetraalkylammonium ylides derived from l-alanine amides proceeds via a double axially chiral intermediate to afford the corresponding α-substituted alanine derivatives with high enantio- and diastereoselectivities.

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Link

http://pubs.rsc.org/en/content/articlepdf/2014/CC/C4CC02536A

Reference31 articles.

1. I. E. Markó , in Comprehensive Organic Synthesis , ed. B. M. Trost and I. Fleming , Pergamon , Oxford , 1991 , ch. 3.10, vol. 3

2. Sigmatropic rearrangements of ‘onium’ ylids

3. Recent advances in the Stevens rearrangement of ammonium ylides. Application to the synthesis of alkaloid natural products

4. Efficient synthesis of optically active α-quaternary amino acids by highly diastereoselective [2,3]-rearrangement of allylic ammonium ylides

5. 1,2-Dimethoxy-4,5-dimethylene: a new protecting group for acyclic amino acid derivatives prepared by Stevens rearrangement

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