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Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for ?-complex instability.

ABSTRACT: Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki-Hiyama methallylations from the alcohol or aldehyde oxidation level via iridium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetate does not react efficiently. Double methallylation of 1,3-propanediol provides the C(2)-symmetric adduct as a single enantiomer, as determined by HPLC analysis.

SUBMITTER: Hassan A

PROVIDER: S-EPMC3225001 | biostudies-other | 2011 Sep

REPOSITORIES: biostudies-other

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Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability.

Hassan Abbas A Townsend Ian A IA Krische Michael J MJ

Chemical communications (Cambridge, England) 20110810 36

Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki-Hiyama methallylations from the alcohol or aldehyde oxidation level via iridium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetate does not react efficiently. Double methallylation of 1,3-propanediol provides the C(2)-symmetric adduct as a single enantiomer, as determined by HPLC analysis. ...[more]

PMID: 21829853

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