Dynamic Kinetic Resolution in Rhodium-Catalyzed Asymmetric Arylation of Phospholene Oxides

The reaction of 2,5-dihydro-1H-phosphole 1-oxide 1 with ArB­(pin) 3 in the presence of a chiral (R)-segphos–rhodium catalyst under highly basic conditions (10 equiv of KOH) gave high yields of (1S,3S)-3-arylphospholane 1-oxide 4 with high diastereoselectivity as well as high enantioselectivity. Equi...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 139; no. 24; pp. 8122 - 8125
Main Authors Lim, Kelvin Meng-Hui, Hayashi, Tamio
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ENZYMATIC RESOLUTION
RING-CLOSING METATHESIS
ENANTIOSELECTIVE SYNTHESIS
COUPLING REACTIONS
ALPHA-KETO ESTERS
ALPHA-(ACYLAMINO)ACRYLIC ACIDS
TRANSFER HYDROGENATION
METAL CATALYSIS
PHOSPHINE OXIDES
STEREOSELECTIVE HYDROGENATION
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Summary:The reaction of 2,5-dihydro-1H-phosphole 1-oxide 1 with ArB­(pin) 3 in the presence of a chiral (R)-segphos–rhodium catalyst under highly basic conditions (10 equiv of KOH) gave high yields of (1S,3S)-3-arylphospholane 1-oxide 4 with high diastereoselectivity as well as high enantioselectivity. Equilibration of 1 with its 2,3-dihydro isomer 2, which is chiral and racemic, by base-catalyzed olefin isomerization followed by kinetic resolution of 2 with the chiral rhodium catalyst realized the present dynamic kinetic resolution.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b04570