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J Am Chem Soc. 2009 May 13;131(18):6354-5. doi: 10.1021/ja902202g.

Double bond isomerization/enantioselective aza-Petasis-Ferrier rearrangement sequence as an efficient entry to anti- and enantioenriched beta-amino aldehydes.

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1
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.

Abstract

Highly anti- and enantioselective synthesis of beta-amino aldehydes having an aliphatic substituent at the beta-position was accomplished by a combination of two catalytic reactions, that is, an initial Ni(II) complex-catalyzed isomerization of a double bond followed by a chiral phosphoric acid catalyzed aza-Petasis-Ferrier rearrangement, using hemiaminal allyl ethers as the initial substrate. The chiral phosphoric acid also functioned as an efficient resolving catalyst of racemic hemiaminal vinyl ethers.

PMID:
19374414
DOI:
10.1021/ja902202g
[Indexed for MEDLINE]
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