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Lewis acid-catalyzed asymmetric radical additions of trialkyl-boranes to (1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyl-2H-azirine-3-carboxylate
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2005 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 61, no 35, 8443-8450 p.Article in journal (Refereed) Published
Abstract [en]

The asymmetric addition of alkyl radicals to (IR,2S,5R)-2-(l-methyl-l-phenylethyl)-5-methylcyclohexyl-2H-azirine-3-carboxylate (1) yielding the corresponding 2-alkylaziridine-2-carboxylates has been investigated. High diastereoselectivities and good yields were obtained in the addition of primary alkyl radicals to azirine 1, while secondary radicals gave a lower dr. The influence of Lewis acids was also investigated, 10 mol% of CuCl were found to increase the dr.

Place, publisher, year, edition, pages
2005. Vol. 61, no 35, 8443-8450 p.
Keyword [en]
azirines, asymmetric radical additions, chiral auxiliaries, glyoxylic oxime ether, alpha-amino-acids, acyclic stereocontrol, chiral aziridines, facile reaction, alkyl radicals, imines, organoboranes, 2h-azirines, efficient
URN: urn:nbn:se:kth:diva-14976DOI: 10.1016/j.tet.2005.06.076ISI: 000231211800016ScopusID: 2-s2.0-23044478223OAI: diva2:333017
QC 20100525Available from: 2010-08-05 Created: 2010-08-05Bibliographically approved

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