Palladium-catalyzed coupling of allyl acetates with aldehyde and imine electrophiles in the presence of Bis(pinacolato)diboron.

[reaction: see text] An efficient one-pot procedure was developed for palladium-catalyzed electrophilic substitution of allyl acetates (2a-h) in the presence of bis(pinacolato)diboron (1). These reactions proceed with an excellent regioselectivity and with a remarkably high stereoselectivity. The catalytic transformations take place via palladium-catalyzed formation of allyl boronates, which subsequently react with aldehyde (3) and sulfon-imine (4) electrophiles to afford homoallylic alcohols (5a-h) and amines (6a-d), respectively. A particularly interesting mechanistic feature is that the allylic substitution of the transient allyl boronate with sulfon-imine requires palladium catalysis. This finding indicates that the formation of the homoallylic amine derivatives (6a-d) involves bis-allylpalladium intermediates.

• Publication year

  2003

• Venue

  Organic Letters

• Publication date

  2003-07-19

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/OL035052IPMID 12916982
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

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