Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 17, Pages 3698-3702Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000010
Keywords
allylic alcohols; asymmetric [2+2+2] cycloaddition; enynes; kinetic resolution; rhodium
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Funding
- JSPS (Japan) [JP26102004]
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It has been established that a cationic rhodium(I)/P-phos complex catalyzes the asymmetric [2+2+2] cycloaddition of 1,6-enynes with racemic secondary allylic alcohols to produce the corresponding chiral bicyclic cyclohexenes, possessing three stereogenic centers, as a single diastereomer with excellent ee values. Mechanistic experiments revealed that the present cycloaddition proceeds through the kinetic resolution of the racemic secondary allylic alcohols, in which one enantiomer preferentially reacts with the 1,6-enyne.
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