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Boron enolate chemistry toward the syntheses of polyketide stereotetrads.
Chem Rec. 2014 Feb; 14(1):52-61.CR

Abstract

In 1976 Mukaiyama published a paper that was to make a major impact on the development of the aldol reaction in the future. Mild enolate formation by treatment of a ketone with dibutylboron triflate in the presence of a tertiary amine generates a relatively stable boron enolate, which can subsequently react with an aldehyde to give the cross-aldol product in good yields. This reaction has become a reliable tool for the practicing synthetic chemist. Nearly 10000 polyketides are known, and of these about 600 contain the tripropionate unit with a stereotetrad, four contiguous stereocenters with alternating methyl and hydroxyl substituents in the main chain. The versatility of the boron enolate aldol reaction is showcased with selected applications in the synthesis of these structural motifs.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Koskinen AM
Aalto University, School of Chemical Technology, Laboratory of Organic Chemistry, PO Box 16100, 00076, Aalto, Finland. ari.koskinen@aalto.fi.

MeSH

AldehydesBoronPolyketidesStereoisomerism

Pub Type(s)

Journal Article

Language

eng

PubMed ID

24420331

Citation

Koskinen, Ari M P.. "Boron Enolate Chemistry Toward the Syntheses of Polyketide Stereotetrads." Chemical Record (New York, N.Y.), vol. 14, no. 1, 2014, pp. 52-61.
Koskinen AM. Boron enolate chemistry toward the syntheses of polyketide stereotetrads. Chem Rec. 2014;14(1):52-61.
Koskinen, A. M. (2014). Boron enolate chemistry toward the syntheses of polyketide stereotetrads. Chemical Record (New York, N.Y.), 14(1), 52-61. https://doi.org/10.1002/tcr.201300033
Koskinen AM. Boron Enolate Chemistry Toward the Syntheses of Polyketide Stereotetrads. Chem Rec. 2014;14(1):52-61. PubMed PMID: 24420331.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Boron enolate chemistry toward the syntheses of polyketide stereotetrads. A1 - Koskinen,Ari M P, PY - 2013/09/29/received PY - 2014/1/15/entrez PY - 2014/1/15/pubmed PY - 2014/10/23/medline KW - aldol reaction KW - boron enolates KW - diastereoselectivity KW - enantioselectivity KW - polyketides SP - 52 EP - 61 JF - Chemical record (New York, N.Y.) JO - Chem Rec VL - 14 IS - 1 N2 - In 1976 Mukaiyama published a paper that was to make a major impact on the development of the aldol reaction in the future. Mild enolate formation by treatment of a ketone with dibutylboron triflate in the presence of a tertiary amine generates a relatively stable boron enolate, which can subsequently react with an aldehyde to give the cross-aldol product in good yields. This reaction has become a reliable tool for the practicing synthetic chemist. Nearly 10000 polyketides are known, and of these about 600 contain the tripropionate unit with a stereotetrad, four contiguous stereocenters with alternating methyl and hydroxyl substituents in the main chain. The versatility of the boron enolate aldol reaction is showcased with selected applications in the synthesis of these structural motifs. SN - 1528-0691 UR - https://www.unboundmedicine.com/medline/citation/24420331/Boron_enolate_chemistry_toward_the_syntheses_of_polyketide_stereotetrads_ DB - PRIME DP - Unbound Medicine ER -