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One-pot enantioselective aziridination of olefins catalyzed by a copper(I) complex of a novel diimine ligand by using PhI(OAc)(2) and sulfonamide as nitrene precursors.
Chemistry. 2006 Jun 02; 12(17):4568-75.C

Abstract

A novel chiral C(2)-symmetric 1,4-diamine with multistereogenic centers at the backbone of the ligand has been synthesized from cheap natural product D-mannitol through multistep transformations. Its diimine derivative (3 a) was found to be highly effective for the enantioselective control of the copper-catalyzed asymmetric aziridination of olefin derivatives with PhI==NTs as the nitrene source, affording the corresponding N-sulfonylated azirindine derivatives in good to excellent yields with up to 99 % ee (ee=enantiomeric excess). The catalyst system discovered in the present work was also extended to a one-pot enantioselective aziridination by using sulfonamide/iodobenzene diacetate as the nitrene source. In this case, most reactions proceeded smoothly to give the corresponding products in moderate yields with good to excellent enantiomeric excesses (75-96 % ee).

Authors+Show Affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China. kding@mail.sioc.ac.cnNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

16598800

Citation

Wang, Xisheng, and Kuiling Ding. "One-pot Enantioselective Aziridination of Olefins Catalyzed By a copper(I) Complex of a Novel Diimine Ligand By Using PhI(OAc)(2) and Sulfonamide as Nitrene Precursors." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 12, no. 17, 2006, pp. 4568-75.
Wang X, Ding K. One-pot enantioselective aziridination of olefins catalyzed by a copper(I) complex of a novel diimine ligand by using PhI(OAc)(2) and sulfonamide as nitrene precursors. Chemistry. 2006;12(17):4568-75.
Wang, X., & Ding, K. (2006). One-pot enantioselective aziridination of olefins catalyzed by a copper(I) complex of a novel diimine ligand by using PhI(OAc)(2) and sulfonamide as nitrene precursors. Chemistry (Weinheim an Der Bergstrasse, Germany), 12(17), 4568-75.
Wang X, Ding K. One-pot Enantioselective Aziridination of Olefins Catalyzed By a copper(I) Complex of a Novel Diimine Ligand By Using PhI(OAc)(2) and Sulfonamide as Nitrene Precursors. Chemistry. 2006 Jun 2;12(17):4568-75. PubMed PMID: 16598800.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - One-pot enantioselective aziridination of olefins catalyzed by a copper(I) complex of a novel diimine ligand by using PhI(OAc)(2) and sulfonamide as nitrene precursors. AU - Wang,Xisheng, AU - Ding,Kuiling, PY - 2006/4/7/pubmed PY - 2007/7/7/medline PY - 2006/4/7/entrez SP - 4568 EP - 75 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 12 IS - 17 N2 - A novel chiral C(2)-symmetric 1,4-diamine with multistereogenic centers at the backbone of the ligand has been synthesized from cheap natural product D-mannitol through multistep transformations. Its diimine derivative (3 a) was found to be highly effective for the enantioselective control of the copper-catalyzed asymmetric aziridination of olefin derivatives with PhI==NTs as the nitrene source, affording the corresponding N-sulfonylated azirindine derivatives in good to excellent yields with up to 99 % ee (ee=enantiomeric excess). The catalyst system discovered in the present work was also extended to a one-pot enantioselective aziridination by using sulfonamide/iodobenzene diacetate as the nitrene source. In this case, most reactions proceeded smoothly to give the corresponding products in moderate yields with good to excellent enantiomeric excesses (75-96 % ee). SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/16598800/One_pot_enantioselective_aziridination_of_olefins_catalyzed_by_a_copper_I__complex_of_a_novel_diimine_ligand_by_using_PhI_OAc__2__and_sulfonamide_as_nitrene_precursors_ L2 - https://doi.org/10.1002/chem.200501109 DB - PRIME DP - Unbound Medicine ER -
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