Literature DB >> 18788743

A highly stereoselective organocatalytic tandem aminoxylation/aza-Michael reaction for the synthesis of tetrahydro-1,2-oxazines.

Di Zhu1, Min Lu, Pei Juan Chua, Bin Tan, Fei Wang, Xinhao Yang, Guofu Zhong.   

Abstract

A facile stereoselective synthesis of multifunctionalized tetrahydro-1,2-oxazines (THOs) has been achieved by the organocatalyzed asymmetric tandem alpha-aminoxylation/aza-Michael reaction for the C-O/C-N bond formations in moderate to good yields with excellent diastereo- (>99:1 dr) and enantioselectivities (92% to >99% ee).

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Year:  2008        PMID: 18788743     DOI: 10.1021/ol801864c

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


  3 in total

1.  A Lewis Acid Catalyzed annulation to 2,1-benzisoxazoles.

Authors:  Kate D Otley; Jonathan A Ellman
Journal:  J Org Chem       Date:  2014-08-26       Impact factor: 4.354

Review 2.  Organocatalyzed asymmetric alpha-oxidation, alpha-aminoxylation and alpha-amination of carbonyl compounds.

Authors:  Tirayut Vilaivan; Worawan Bhanthumnavin
Journal:  Molecules       Date:  2010-02-11       Impact factor: 4.411

3.  Organocatalytic cascade aza-Michael/hemiacetal reaction between disubstituted hydrazines and α,β-unsaturated aldehydes: Highly diastereo- and enantioselective synthesis of pyrazolidine derivatives.

Authors:  Zhi-Cong Geng; Jian Chen; Ning Li; Xiao-Fei Huang; Yong Zhang; Ya-Wen Zhang; Xing-Wang Wang
Journal:  Beilstein J Org Chem       Date:  2012-10-09       Impact factor: 2.883

  3 in total

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