ArticleOrganic letters2008
Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexoses.
Article in Organic letters, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed.
- Highly Stereoselective Addition of β-Borylenamides to Aldehydes Enabled by Late‑Stage Ligand Modification.Angewandte Chemie (International ed. in English) · 2026Article
- Correction: Synthesis of vinyl-substituted alcohols using acetylene as a C2 building block.Chemical science · 2023Article
- Enantioselective Metal-Catalyzed Reductive Coupling of Alkynes with Carbonyl Compounds and Imines: Convergent Construction of Allylic Alcohols and Amines.ACS catalysis · 2022Article
- Cu-catalyzed carboboration of acetylene with Michael acceptors.Chemical science · 2022Article
- Diverse synthesis of C2-linked functionalized molecules via molecular glue strategy with acetylene.Nature communications · 2022Article
- Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.Journal of the American Chemical Society · 2021Article
- From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.ACS catalysis · 2021Article
- Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Synthesis of the C(1)-C(13) Fragment of Leiodermatolide via Hydrogen-Mediated C-C Bond Formation.Organic letters · 2017Article
- Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.Journal of the American Chemical Society · 2016Article
- Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.RSC advances · 2016Article
- A Metallacycle Fragmentation Strategy for Vinyl Transfer from Enol Carboxylates to Secondary Alcohol C-H Bonds via Osmium- or Ruthenium-Catalyzed Transfer Hydrogenation.Journal of the American Chemical Society · 2015Article
- Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.Chemistry (Weinheim an der Bergstrasse, Germany) · 2014Article
- Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenation.Journal of the American Chemical Society · 2013Article
- Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation.Angewandte Chemie (International ed. in English) · 2013Article
- Iridium-catalyzed allylation of chiral β-stereogenic alcohols: bypassing discrete formation of epimerizable aldehydes.Organic letters · 2012Article
- Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective Methods.Organic process research & development · 2011Article
- Alkyne-aldehyde reductive C-C coupling through ruthenium-catalyzed transfer hydrogenation: direct regio- and stereoselective carbonyl vinylation to form trisubstituted allylic alcohols in the absence of premetallated reagents.Chemistry (Weinheim an der Bergstrasse, Germany) · 2011Article
- Total synthesis of bryostatin 7 via C-C bond-forming hydrogenation.Journal of the American Chemical Society · 2011Article
- Iridium-catalyzed anti-diastereo- and enantioselective carbonyl (α-trifluoromethyl)allylation from the alcohol or aldehyde oxidation level.Angewandte Chemie (International ed. in English) · 2011Article
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3 authors.
Funding
Abstract
Hydrogenative coupling of acetylene to alpha-chiral aldehydes 1a-4a using enantiomeric rhodium catalysts ligated by (S)-MeO-BIPHEP and (R)-MeO-BIPHEP delivers the diastereomeric products of carbonyl-(Z)-butadienylation 1b-4b and 1c-4c, respectively, with good to excellent levels of catalyst directed diastereofacial selectivity. Diastereomeric L-glyceraldehyde acetonide adducts 1b and 1c were converted to the four isomeric enoates 6b, 8b, 6c, and 8c, representing a formal synthesis of all eight L-hexoses.
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