Literature DB >> 17407353

Asymmetric thio-Michael/nucleophilic addition domino reaction with chiral N-sulfinimines.

Akio Kamimura1, Hidenori Okawa, Yuki Morisaki, Shingo Ishikawa, Hidemitsu Uno.   

Abstract

Optically active N-sulfinimines underwent stereoselective Michael/nucleophilic addition domino reaction triggered by magnesium thiolate to give alpha-phenylthiomethyl-beta-(N-sulfinylamino) esters in high diastereomeric excess. The adducts were readily converted into optically active alpha-methylene-beta-(N-sulfinylamino)esters so that this reaction provides a useful asymmetric aza-Baylis-Hillman-equivalent method.

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Year:  2007        PMID： 17407353     DOI： 10.1021/jo062251h

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  3 in total

1.  Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters.

Authors:  Franklin A Davis; Hui Qiu; Minsoo Song; Narendra V Gaddiraju
Journal:  J Org Chem       Date:  2009-04-03       Impact factor: 4.354

Review 2.  Applications of aryl-sulfinamides in the synthesis of N-heterocycles.

Authors:  Rose Mary Philip; G S Susan Treesa; Salim Saranya; Gopinathan Anilkumar
Journal:  RSC Adv       Date:  2021-06-08       Impact factor: 4.036

3.  Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction.

Authors:  Koichiro Miyazaki; Yu Yamane; Ryuichiro Yo; Hidemitsu Uno; Akio Kamimura
Journal:  Beilstein J Org Chem       Date:  2013-07-04       Impact factor: 2.883
  3 in total

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