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Palladium‐Catalyzed Cyclopropanation of Strained Alkenes with 3‐Pinacolatoboryl‐1‐arylallyl Carboxylates
Author(s) -
Horino Yoshikazu,
Takahashi Yu,
Kobayashi Ryota,
Abe Hitoshi
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403284
Subject(s) - cyclopropanation , chemistry , palladium , catalysis , molecular sieve , organic chemistry
The palladium‐catalyzed cyclopropanation of strained alkenes with 3‐pinacolatoboryl‐1‐arylallyl carboxylates was explored. The reactions proceeded smoothly under mild conditions, and the cyclopropanation products were obtained in good to high yields with high diastereoselectivities if CsF, 18‐crown‐6, and molecular sieves were used as additives. The reaction was hypothesized to proceed through the formation of a putative palladacyclobutene intermediate that needed to be considered to explain the observed stereochemistry.