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Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey-Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines.
Org Lett. 2016 Feb 05; 18(3):532-5.OL

Abstract

A general and direct strategy for the synthesis of chiral spiro-aziridine oxindoles has been developed via an aza-Corey-Chaykovsky reaction of isatin-derived N-tert-butanesulfinyl ketimines with excellent selectivity (dr = 98:2 to >99:1). The method is explored for the synthesis of chiral 3-substituted spiro-aziridine oxindoles with high (2S,3S)-selectivity over (2S,3R).

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Publisher Full Text (DOI)

Authors+Show Affiliations

Hajra S
Centre of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus , Raebareli Road, Lucknow 226014, India.
Aziz SM
Department of Chemistry, Indian Institute of Technology Kharagpur , Kharagpur 721302, India.
Jana B
Centre of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus , Raebareli Road, Lucknow 226014, India. Department of Chemistry, Indian Institute of Technology Kharagpur , Kharagpur 721302, India.
Mahish P
Centre of Biomedical Research, Sanjay Gandhi Post-Graduate Institute of Medical Sciences Campus , Raebareli Road, Lucknow 226014, India. Department of Chemistry, Indian Institute of Technology Kharagpur , Kharagpur 721302, India.
Das D
Department of Chemistry, Indian Institute of Technology Kharagpur , Kharagpur 721302, India.

MeSH

AziridinesCatalysisIminesIndolesIsatinMolecular StructureNitrilesOxindolesStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

26781920

Citation

Hajra, Saumen, et al. "Synthesis of Chiral Spiro-Aziridine Oxindoles Via Aza-Corey-Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines." Organic Letters, vol. 18, no. 3, 2016, pp. 532-5.
Hajra S, Aziz SM, Jana B, et al. Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey-Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines. Org Lett. 2016;18(3):532-5.
Hajra, S., Aziz, S. M., Jana, B., Mahish, P., & Das, D. (2016). Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey-Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines. Organic Letters, 18(3), 532-5. https://doi.org/10.1021/acs.orglett.5b03564
Hajra S, et al. Synthesis of Chiral Spiro-Aziridine Oxindoles Via Aza-Corey-Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines. Org Lett. 2016 Feb 5;18(3):532-5. PubMed PMID: 26781920.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of Chiral Spiro-Aziridine Oxindoles via Aza-Corey-Chaykovsky Reaction of Isatin Derived N-tert-Butanesulfinyl Ketimines. AU - Hajra,Saumen, AU - Aziz,Sk Mohammad, AU - Jana,Bibekananda, AU - Mahish,Prosenjit, AU - Das,Dhiraj, Y1 - 2016/01/19/ PY - 2016/1/20/entrez PY - 2016/1/20/pubmed PY - 2016/6/21/medline SP - 532 EP - 5 JF - Organic letters JO - Org Lett VL - 18 IS - 3 N2 - A general and direct strategy for the synthesis of chiral spiro-aziridine oxindoles has been developed via an aza-Corey-Chaykovsky reaction of isatin-derived N-tert-butanesulfinyl ketimines with excellent selectivity (dr = 98:2 to >99:1). The method is explored for the synthesis of chiral 3-substituted spiro-aziridine oxindoles with high (2S,3S)-selectivity over (2S,3R). SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/26781920/Synthesis_of_Chiral_Spiro_Aziridine_Oxindoles_via_Aza_Corey_Chaykovsky_Reaction_of_Isatin_Derived_N_tert_Butanesulfinyl_Ketimines_ DB - PRIME DP - Unbound Medicine ER -
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