A tandem non-aldol aldol Mukaiyama aldol reaction.
Org Lett. 2003 Nov 27; 5(24):4705-7.OL

Abstract

[reaction: see text] A new one-pot tandem aldol process is described in which a secondary epoxy silyl ether is converted into the 1,5-bis-silyloxy-3-alkanone in good yield. Thus, treatment of the epoxy silyl ether 8 with TBSOTf and base affords the silyl enol ether 9 via non-aldol aldol rearrangement and addition of benzaldehyde and TBSOTf gives the ketone 10 with 4:1 syn selectivity. The diastereoselectivity changes to an anti preference for most aldehydes. This anti selectivity overwhelms the normal Felkin-Ahn preference; namely, the 1,5-anti isomer predominates even when it is anti-Felkin-Ahn.

Authors+Show Affiliations

Jung ME

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA. jung@chem.ucla.edu

van den Heuvel A

No affiliation info available

MeSH

AldehydesEpoxy CompoundsEthersKetonesMolecular StructureSilanesStereoisomerism

Pub Type(s)

Journal Article

Research Support, U.S. Gov't, Non-P.H.S.

Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

14627420

Citation

Jung, Michael E., and Alexandra van den Heuvel. "A Tandem Non-aldol Aldol Mukaiyama Aldol Reaction." Organic Letters, vol. 5, no. 24, 2003, pp. 4705-7.

Jung ME, van den Heuvel A. A tandem non-aldol aldol Mukaiyama aldol reaction. Org Lett. 2003;5(24):4705-7.

Jung, M. E., & van den Heuvel, A. (2003). A tandem non-aldol aldol Mukaiyama aldol reaction. Organic Letters, 5(24), 4705-7.

Jung ME, van den Heuvel A. A Tandem Non-aldol Aldol Mukaiyama Aldol Reaction. Org Lett. 2003 Nov 27;5(24):4705-7. PubMed PMID: 14627420.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - A tandem non-aldol aldol Mukaiyama aldol reaction. AU - Jung,Michael E, AU - van den Heuvel,Alexandra, PY - 2003/11/25/pubmed PY - 2004/5/25/medline PY - 2003/11/25/entrez SP - 4705 EP - 7 JF - Organic letters JO - Org Lett VL - 5 IS - 24 N2 - [reaction: see text] A new one-pot tandem aldol process is described in which a secondary epoxy silyl ether is converted into the 1,5-bis-silyloxy-3-alkanone in good yield. Thus, treatment of the epoxy silyl ether 8 with TBSOTf and base affords the silyl enol ether 9 via non-aldol aldol rearrangement and addition of benzaldehyde and TBSOTf gives the ketone 10 with 4:1 syn selectivity. The diastereoselectivity changes to an anti preference for most aldehydes. This anti selectivity overwhelms the normal Felkin-Ahn preference; namely, the 1,5-anti isomer predominates even when it is anti-Felkin-Ahn. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/14627420/A_tandem_non_aldol_aldol_Mukaiyama_aldol_reaction_ DB - PRIME DP - Unbound Medicine ER -

Tags

A tandem non-aldol aldol Mukaiyama aldol reaction.Org Lett. 2003 Nov 27; 5(24):4705-7.OL