TY - JOUR
T1 - Palladium-Catalyzed Hydroboration/Cyclization of 1, n-Dienes
AU - Kanno, Shota
AU - Kakiuchi, Fumitoshi
AU - Kochi, Takuya
N1 - Funding Information:
This work was supported, in part, by JSPS KAKENHI Grants 18H01985 (Grant-in-Aid for Scientific Research (B)) and 22H02085 (Grant-in-Aid for Scientific Research (B)). S.K. is also grateful for support from the Japan Society for the Promotion of Science (JSPS) for a Research Fellowship for Young Scientists (JP22J13075).
Publisher Copyright:
© 2023 American Chemical Society.
PY - 2022
Y1 - 2022
N2 - While the hydroboration of alkenes is well established, the corresponding cyclization reaction of dienes remains challenging. Here, we report a new method for hydroboration/cyclization applicable to various 1,n-dienes and hydroboranes. The method features the direct synthesis of borylalkyl cyclopentanes from common 1,6-dienes, which is highlighted by syntheses of elaborated pyrrolidine cores from easily accessible diallylamines. Notably, 1,n-dienes (n > 6) also undergo five-membered ring formation, offering "remote"hydroboration/cyclization that would be otherwise difficult to achieve.
AB - While the hydroboration of alkenes is well established, the corresponding cyclization reaction of dienes remains challenging. Here, we report a new method for hydroboration/cyclization applicable to various 1,n-dienes and hydroboranes. The method features the direct synthesis of borylalkyl cyclopentanes from common 1,6-dienes, which is highlighted by syntheses of elaborated pyrrolidine cores from easily accessible diallylamines. Notably, 1,n-dienes (n > 6) also undergo five-membered ring formation, offering "remote"hydroboration/cyclization that would be otherwise difficult to achieve.
UR - http://www.scopus.com/inward/record.url?scp=85147161944&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85147161944&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.2c02781
DO - 10.1021/acs.joc.2c02781
M3 - Article
AN - SCOPUS:85147161944
SN - 0022-3263
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
ER -