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The impact of the Mukaiyama aldol reaction in total synthesis.
Angew Chem Int Ed Engl. 2013 Aug 26; 52(35):9097-108.AC

Abstract

Four decades since Mukaiyama's first reports on the successful application of silicon and boron enolates in directed aldol reactions, the ability of this highly controlled carbon-carbon bond-forming method to simultaneously define stereochemistry, introduce complexity, and construct the carbon skeleton with a characteristic 1,3-oxygenation pattern has made it a powerful tool for natural product synthesis. This Minireview highlights a number of representative total syntheses that demonstrate the impact of the Mukaiyama aldol reaction and discusses the underlying mechanistic rationale that determines the stereochemical outcomes.

Authors+Show Affiliations

Laboratory of Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502, Japan.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Review

Language

eng

PubMed ID

23893491

Citation

Kan, S B Jennifer, et al. "The Impact of the Mukaiyama Aldol Reaction in Total Synthesis." Angewandte Chemie (International Ed. in English), vol. 52, no. 35, 2013, pp. 9097-108.
Kan SB, Ng KK, Paterson I. The impact of the Mukaiyama aldol reaction in total synthesis. Angew Chem Int Ed Engl. 2013;52(35):9097-108.
Kan, S. B., Ng, K. K., & Paterson, I. (2013). The impact of the Mukaiyama aldol reaction in total synthesis. Angewandte Chemie (International Ed. in English), 52(35), 9097-108. https://doi.org/10.1002/anie.201303914
Kan SB, Ng KK, Paterson I. The Impact of the Mukaiyama Aldol Reaction in Total Synthesis. Angew Chem Int Ed Engl. 2013 Aug 26;52(35):9097-108. PubMed PMID: 23893491.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The impact of the Mukaiyama aldol reaction in total synthesis. AU - Kan,S B Jennifer, AU - Ng,Kenneth K-H, AU - Paterson,Ian, Y1 - 2013/07/26/ PY - 2013/05/07/received PY - 2013/7/30/entrez PY - 2013/7/31/pubmed PY - 2014/3/13/medline KW - aldol reaction KW - enolates KW - natural products KW - polyketides KW - stereocontrol SP - 9097 EP - 108 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 52 IS - 35 N2 - Four decades since Mukaiyama's first reports on the successful application of silicon and boron enolates in directed aldol reactions, the ability of this highly controlled carbon-carbon bond-forming method to simultaneously define stereochemistry, introduce complexity, and construct the carbon skeleton with a characteristic 1,3-oxygenation pattern has made it a powerful tool for natural product synthesis. This Minireview highlights a number of representative total syntheses that demonstrate the impact of the Mukaiyama aldol reaction and discusses the underlying mechanistic rationale that determines the stereochemical outcomes. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/23893491/The_impact_of_the_Mukaiyama_aldol_reaction_in_total_synthesis_ L2 - https://doi.org/10.1002/anie.201303914 DB - PRIME DP - Unbound Medicine ER -
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