Literature DB >> 19239262

Synthesis of aminocyclobutanes through ring expansion of N-vinyl-beta-lactams.

Lawrence L W Cheung1, Andrei K Yudin.   

Abstract

Both eight-membered enamide rings and fused [4.2.0]aminocyclobutane-containing delta-lactams can be accessed from N-vinyl-beta-lactams. The eight-membered rings are made through a [3,3] sigmatropic rearrangement. At elevated temperature, the eight-membered lactam undergoes electrocyclization to furnish fused cyclobutane delta-lactams in a diastereoselective manner.

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Year:  2009        PMID： 19239262     DOI： 10.1021/ol900118d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  5 in total

1.  An Efficient Synthesis of de novo Imidates via Aza-Claisen Rearrangements of N-Allyl Ynamides.

Authors:  Kyle A Dekorver; Troy D North; Richard P Hsung
Journal:  Synlett       Date:  2010-10       Impact factor: 2.454

2.  A divergent mechanistic course of Pd(0)-catalyzed aza-Claisen rearrangement and aza-Rautenstrauch-type cyclization of N-allyl ynamides.

Authors:  Kyle A Dekorver; Richard P Hsung; Andrew G Lohse; Yu Zhang
Journal:  Org Lett       Date:  2010-04-16       Impact factor: 6.005

3.  N-allyl-N-sulfonyl ynamides as synthetic precursors to amidines and vinylogous amidines. An unexpected N-to-C 1,3-sulfonyl shift in nitrile synthesis.

Authors:  Kyle A DeKorver; Whitney L Johnson; Yu Zhang; Richard P Hsung; Huifang Dai; Jun Deng; Andrew G Lohse; Yan-Shi Zhang
Journal:  J Org Chem       Date:  2011-05-24       Impact factor: 4.354

4.  A Convenient Synthesis of γ-Amino-Ynamides via Additions of Lithiated Ynamides to Aryl Imines. Observation of an Aza-Meyer-Schuster Rearrangement.

Authors:  Rui Qi; Xiao-Na Wang; Kyle A Dekorver; Yu Tang; Chao-Chao Wang; Qian Li; Hui Li; Ming-Can Lv; Qing Yu; Richard P Hsung
Journal:  Synthesis (Stuttg)       Date:  2013-07-01       Impact factor: 3.157

5.  Metal-free syntheses of new azocines via addition reactions of enaminones with acenaphthoquinone followed by oxidative cleavages of the corresponding vicinal diols.

Authors:  S Hekmat Mousavi; Mohammad Reza Mohammadizadeh; Satoru Arimitsu; Dariush Saberi; Samira Poorsadeghi; Kojya Genta
Journal:  RSC Adv       Date:  2020-05-29       Impact factor: 4.036
  5 in total

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