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Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction.
Org Lett. 2005 Dec 08; 7(25):5657-60.OL

Abstract

[chemical reaction: see text]. The concept of hydrogen bonding catalysis was extended to the vinylogous Mukaiyama aldol reaction, which gives rapid access to polyketide derivatives. The reaction of the silyldienol ether shown and a range of aldehydes catalyzed by TADDOL proceeds regiospecifically to produce the addition products in good yields and enantiomeric excesses.

Links

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Authors+Show Affiliations

Gondi VB
Department of Chemistry, The University of Chicago, Chicago, Illinois 60637, USA.
Gravel M
No affiliation info available
Rawal VH
No affiliation info available

MeSH

AldehydesCatalysisHydrogen BondingMacrolidesModels, MolecularMolecular StructureSilanesStereoisomerism

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

16321015

Citation

Gondi, Vijaya Bhasker, et al. "Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction." Organic Letters, vol. 7, no. 25, 2005, pp. 5657-60.
Gondi VB, Gravel M, Rawal VH. Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction. Org Lett. 2005;7(25):5657-60.
Gondi, V. B., Gravel, M., & Rawal, V. H. (2005). Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction. Organic Letters, 7(25), 5657-60.
Gondi VB, Gravel M, Rawal VH. Hydrogen Bond Catalyzed Enantioselective Vinylogous Mukaiyama Aldol Reaction. Org Lett. 2005 Dec 8;7(25):5657-60. PubMed PMID: 16321015.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Hydrogen bond catalyzed enantioselective vinylogous Mukaiyama aldol reaction. AU - Gondi,Vijaya Bhasker, AU - Gravel,Michel, AU - Rawal,Viresh H, PY - 2005/12/3/pubmed PY - 2006/8/29/medline PY - 2005/12/3/entrez SP - 5657 EP - 60 JF - Organic letters JO - Org Lett VL - 7 IS - 25 N2 - [chemical reaction: see text]. The concept of hydrogen bonding catalysis was extended to the vinylogous Mukaiyama aldol reaction, which gives rapid access to polyketide derivatives. The reaction of the silyldienol ether shown and a range of aldehydes catalyzed by TADDOL proceeds regiospecifically to produce the addition products in good yields and enantiomeric excesses. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16321015/Hydrogen_bond_catalyzed_enantioselective_vinylogous_Mukaiyama_aldol_reaction_ DB - PRIME DP - Unbound Medicine ER -