ArticleJournal of the American Chemical Society2012
Highly stereoselective synthesis of anti,anti-dipropionate stereotriads: a solution to the long-standing problem of challenging mismatched double asymmetric crotylboration reactions.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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17 citing papers in PubMed.
- Asymmetric Ketone Diene Coupling via Stereodivergent Copper Catalysis.Journal of the American Chemical Society · 2026Article
- Enantioselective Butadiene-Mediated Aldehyde Crotylation of Alcohol Proelectrophiles: RuHCl(CO)(PPhOrganic letters · 2026Article
- Iterative Catalyst-Controlled Diastereoselective Matteson Homologations Enable the Selective Synthesis of Benzestrol Isomers.Journal of the American Chemical Society · 2024Article
- Cornforth-Evans Transition States in Stereocontrolled Allylborations of Epoxy Aldehydes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.Chemical science · 2020Article
- Ruthenium-catalysed multicomponent synthesis of the 1,3-dienyl-6-oxy polyketide motif.Nature chemistry · 2020Article
- (Chemical science · 2019Article
- Iterative assembly line synthesis of polypropionates with full stereocontrol.Nature chemistry · 2017Article
- Asymmetric Synthesis of Dipropionate Derivatives through Catalytic Hydrogenation of EnantioenrichedSynthesis · 2016Article
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- Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.Journal of the American Chemical Society · 2013Article
- Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.Organic letters · 2013Article
- Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.Organic letters · 2013Article
- Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.The Journal of organic chemistry · 2013Article
- Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.Journal of the American Chemical Society · 2012Article
- Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction.Organic letters · 2012Article
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2 authors.
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Abstract
The stereocontrolled synthesis of the β-branched anti,anti-dipropionate stereotriad 4 via aldol or crotylmetal chemistry represents a historical challenge to the organic synthesis community. Here we describe a general solution to the long-standing problem associated with the synthesis of 4 by utilizing mismatched double asymmetric crotylboration reactions of enantioenriched α-methyl substituted aldehydes with the chiral, nonracemic crotylborane reagent (S)-(E)-22 (or its enantiomer). This method not only provides direct access to anti,anti-dipropionate stereotriads 24 [a synthetic equivalent of 4] with very good (5-8:1) if not excellent (≥15:1) diastereoselectivity from β-branched chiral aldehydes with ≤50:1 intrinsic diastereofacial selectivity preferences but also provides a vinylstannane unit in the products that is properly functionalized for use in subsequent C-C bond-forming events. We anticipate that this method will be widely applicable and will lead to substantial simplification of strategies for synthesis of polyketide natural products.
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