Stereochemistry of intermolecular oxypalladation: Pd(II)-catalyzed 1,3-chirality transfer reaction of chiral allylic alcohol with methanol.


The intermolecular oxypalladation of chiral nonracemic allylic alcohols (S)-1, (R)-1, and (R)-3 in methanol gave chiral nonracemic methyl allyl ethers (S)-2 and/or (R)-2 with excellent selectivity. The reaction induced the 1,3-chirality transfer to give syn-S(N)2' product exclusively through syn oxypalladation. On the other hand, the anti-S(N)2' product was… (More)
DOI: 10.1021/jo9011464