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Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of syn-sec,tert-Diols via (Z)-σ-Allylmetal Intermediates.

ABSTRACT: The first catalytic enantioselective ruthenium-catalyzed carbonyl reductive couplings of allene pronucleophiles is described. Using an iodide-modified ruthenium-BINAP-catalyst and O-benzhydryl alkoxyallene 1a, carbonyl (α-alkoxy)allylation occurs from the alcohol or aldehyde oxidation level to form enantiomerically enriched syn-sec,tert-diols. Internal chelation directs intervention of (Z)-σ-alkoxyallylruthenium isomers, which engage in stereospecific carbonyl addition.

SUBMITTER: Xiang M 

PROVIDER: S-EPMC8299538 | biostudies-literature | 2021 Jun

REPOSITORIES: biostudies-literature

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Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of <i>syn-sec,tert</i>-Diols via (<i>Z</i>)-σ-Allylmetal Intermediates.

Xiang Ming M   Pfaffinger Dana E DE   Ortiz Eliezer E   Brito Gilmar A GA   Krische Michael J MJ  

Journal of the American Chemical Society 20210601 23

The first catalytic enantioselective ruthenium-catalyzed carbonyl reductive couplings of allene pronucleophiles is described. Using an iodide-modified ruthenium-BINAP-catalyst and <i>O</i>-benzhydryl alkoxyallene <b>1a</b>, carbonyl (α-alkoxy)allylation occurs from the alcohol or aldehyde oxidation level to form enantiomerically enriched <i>syn</i>-<i>sec,tert</i>-diols. Internal chelation directs intervention of (<i>Z</i>)-σ-alkoxyallylruthenium isomers, which engage in stereospecific carbonyl  ...[more]

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