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Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions.
Org Lett. 2001 Nov 01; 3(22):3561-4.OL

Abstract

[reaction: see text]. The use of the Z-configured vinylogous silyl ketene acetals in Mukaiyama aldol reactions is described. Isopropyl alcohol as scavanger and the use of tris(pentafluorophenyl)borane as the Lewis acid are required for obtaining the gamma-alkylated syn-product selectively. In cases of alpha-chiral aldehydes, Felkin-Anh selectivity was observed.

Authors+Show Affiliations

Hassfeld J
Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany.
Christmann M
No affiliation info available
Kalesse M
No affiliation info available

MeSH

2-PropanolAcetalsAldehydesBoranesCatalysisEthylenesIndicators and ReagentsKetonesMagnetic Resonance SpectroscopyStereoisomerism

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

11678708

Citation

Hassfeld, J, et al. "Rapid Access to Polyketide Scaffolds Via Vinylogous Mukaiyama Aldol Reactions." Organic Letters, vol. 3, no. 22, 2001, pp. 3561-4.
Hassfeld J, Christmann M, Kalesse M. Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions. Org Lett. 2001;3(22):3561-4.
Hassfeld, J., Christmann, M., & Kalesse, M. (2001). Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions. Organic Letters, 3(22), 3561-4.
Hassfeld J, Christmann M, Kalesse M. Rapid Access to Polyketide Scaffolds Via Vinylogous Mukaiyama Aldol Reactions. Org Lett. 2001 Nov 1;3(22):3561-4. PubMed PMID: 11678708.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions. AU - Hassfeld,J, AU - Christmann,M, AU - Kalesse,M, PY - 2001/10/27/pubmed PY - 2002/1/5/medline PY - 2001/10/27/entrez SP - 3561 EP - 4 JF - Organic letters JO - Org Lett VL - 3 IS - 22 N2 - [reaction: see text]. The use of the Z-configured vinylogous silyl ketene acetals in Mukaiyama aldol reactions is described. Isopropyl alcohol as scavanger and the use of tris(pentafluorophenyl)borane as the Lewis acid are required for obtaining the gamma-alkylated syn-product selectively. In cases of alpha-chiral aldehydes, Felkin-Anh selectivity was observed. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/11678708/Rapid_access_to_polyketide_scaffolds_via_vinylogous_Mukaiyama_aldol_reactions_ L2 - https://doi.org/10.1021/ol016677o DB - PRIME DP - Unbound Medicine ER -