Concomitant C(α),C(β)-asymmetric induction in the aza-Claisen rearrangement of N-allylketene N,O-acetals

Mark J. Kurth, Owen H W Decker

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Abstract

Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetals 4 is described. The starting materials, allylic alkylating agent 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5/7/9 in 97-98% enantiomeric excess and with 79-92% diastereoselectivity. The overall yields for this process (2 → 5/7/9) range from 73 to 87%. A combination of excellent N,O-acetal face selectivity, excellent (Z)-ketene N,O-acetal olefin selectivity, and moderate chair selectivity are shown to account for the observed diastereoselectivity.

Original languageEnglish (US)
Pages (from-to)1377-1383
Number of pages7
JournalJournal of Organic Chemistry
Volume51
Issue number9
StatePublished - 1986

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Acetals
Alkylating Agents
Alkenes

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  • Organic Chemistry

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Concomitant C(α),C(β)-asymmetric induction in the aza-Claisen rearrangement of N-allylketene N,O-acetals. / Kurth, Mark J.; Decker, Owen H W.

In: Journal of Organic Chemistry, Vol. 51, No. 9, 1986, p. 1377-1383.

Research output: Contribution to journalArticle

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abstract = "Asymmetric C-C bond formation via the diastereoselective aza-Claisen rearrangement of N-allylketene N,O-acetals 4 is described. The starting materials, allylic alkylating agent 1 and optically pure oxazoline 2, are easily prepared and, in a one-pot procedure, generate rearranged oxazolines 5/7/9 in 97-98{\%} enantiomeric excess and with 79-92{\%} diastereoselectivity. The overall yields for this process (2 → 5/7/9) range from 73 to 87{\%}. A combination of excellent N,O-acetal face selectivity, excellent (Z)-ketene N,O-acetal olefin selectivity, and moderate chair selectivity are shown to account for the observed diastereoselectivity.",
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