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Enantiopure trans -4,5-disubstituted 2-imidazolidinones via copper(I)-catalyzed ring opening of 1,1′-DiBoc-2,2′-biaziridine with Grignard reagents

Journal Article


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Abstract


  • The copper-catalyzed ring opening of chiral-pool-derived 1,1′-diBoc-2,2′-biaziridine with Grignard reagents affords enantiopure 2-imidazolidinones in a desymmetrizing, cascade process involving the Boc protecting group. This divergent strategy provides reaction-ready, N-differentiated products and allows two C–C bond constructions concurrent to imidazolidinone formation. A variety of alkyl, cyclic, and aryl Grignard reagents are tolerated in reasonable to good yields.

Publication Date


  • 2015

Citation


  • Kennedy, M. D., Bailey, S. J., Wales, S. M. & Keller, P. A. (2015). Enantiopure trans -4,5-disubstituted 2-imidazolidinones via copper(I)-catalyzed ring opening of 1,1′-DiBoc-2,2′-biaziridine with Grignard reagents. Journal of Organic Chemistry, 80 (11), 5992-5998.

Scopus Eid


  • 2-s2.0-84930684856

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4025&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3003

Number Of Pages


  • 6

Start Page


  • 5992

End Page


  • 5998

Volume


  • 80

Issue


  • 11

Abstract


  • The copper-catalyzed ring opening of chiral-pool-derived 1,1′-diBoc-2,2′-biaziridine with Grignard reagents affords enantiopure 2-imidazolidinones in a desymmetrizing, cascade process involving the Boc protecting group. This divergent strategy provides reaction-ready, N-differentiated products and allows two C–C bond constructions concurrent to imidazolidinone formation. A variety of alkyl, cyclic, and aryl Grignard reagents are tolerated in reasonable to good yields.

Publication Date


  • 2015

Citation


  • Kennedy, M. D., Bailey, S. J., Wales, S. M. & Keller, P. A. (2015). Enantiopure trans -4,5-disubstituted 2-imidazolidinones via copper(I)-catalyzed ring opening of 1,1′-DiBoc-2,2′-biaziridine with Grignard reagents. Journal of Organic Chemistry, 80 (11), 5992-5998.

Scopus Eid


  • 2-s2.0-84930684856

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4025&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3003

Number Of Pages


  • 6

Start Page


  • 5992

End Page


  • 5998

Volume


  • 80

Issue


  • 11