Literature DB >> 24328041

1,5-Rhodium shift in rearrangement of N-arenesulfonylazetidin-3-ols into benzosultams.

Naoki Ishida1, Yasuhiro Shimamoto, Takaaki Yano, Masahiro Murakami.   

Abstract

Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

Entities:  

Year:  2013        PMID： 24328041     DOI： 10.1021/ja410910s

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  3 in total

1.  Rhodium(i)-catalyzed asymmetric [4 + 2] cycloaddition reactions of 2-alkylenecyclobutanols with cyclic enones through C-C bond cleavage: efficient access to trans-bicyclic compounds.

Authors:  Xinxin Zheng; Rui Guo; Guozhu Zhang; Dayong Zhang
Journal:  Chem Sci       Date:  2018-01-08       Impact factor: 9.825

2.  Rhodium(i)-catalyzed stereoselective [4+2] cycloaddition of oxetanols with alkynes through C(sp3)-C(sp3) bond cleavage.

Authors:  Rui Guo; Xinxin Zheng; Dayong Zhang; Guozhu Zhang
Journal:  Chem Sci       Date:  2017-01-23       Impact factor: 9.825

3.  Peptide-guided functionalization and macrocyclization of bioactive peptidosulfonamides by Pd(II)-catalyzed late-stage C-H activation.

Authors:  Jian Tang; Hongfei Chen; Yadong He; Wangjian Sheng; Qingqing Bai; Huan Wang
Journal:  Nat Commun       Date:  2018-08-23       Impact factor: 14.919
  3 in total

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