Literature DB >> 20429535

Chiral Brønsted acid catalyzed enantioselective addition of alpha-isocyanoacetamides to aldehydes.

Xiaofei Zeng1, Kehan Ye, Min Lu, Pei Juan Chua, Bin Tan, Guofu Zhong.   

Abstract

A clean and highly efficient enantioselective addition of alpha-isocyanoacetamides to aliphatic aldehydes catalyzed by chiral phosphoric acid in the presence of MS 5 A in toluene at -40 degrees C was developed. Excellent yields (85-98%) and good to excellent enantioselectivities (up to >99% ee) were achieved.

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Year:  2010        PMID： 20429535     DOI： 10.1021/ol1007789

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


  5 in total

1.  Enantioselective synthesis of α-oxy amides via Umpolung amide synthesis.

Authors:  Matthew W Leighty; Bo Shen; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2012-09-11       Impact factor: 15.419

2.  A N,N'-dioxide/Mg(OTf)2 complex catalyzed enantioselective α-addition of isocyanides to alkylidene malonates.

Authors:  Weiwei Luo; Xiao Yuan; Lili Lin; Pengfei Zhou; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2016-04-22       Impact factor: 9.825

3.  Passerini-type reaction of boronic acids enables α-hydroxyketones synthesis.

Authors:  Kai Yang; Feng Zhang; Tongchang Fang; Chaokun Li; Wangyang Li; Qiuling Song
Journal:  Nat Commun       Date:  2021-01-19       Impact factor: 14.919

Review 4.  The 100 facets of the Passerini reaction.

Authors:  Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Chem Sci       Date:  2021-09-30       Impact factor: 9.825

5.  Silica gel-immobilised chiral 1,2-benzenedisulfonimide: a Brønsted acid heterogeneous catalyst for enantioselective multicomponent Passerini reaction.

Authors:  Achille Antenucci; Francesco Marra; Stefano Dughera
Journal:  RSC Adv       Date:  2021-07-29       Impact factor: 4.036
  5 in total

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