TY - JOUR
T1 - Cyclization of 1, n-enynes initiated by the addition reaction of gem-dichromiomethane reagents to alkynes
AU - Murai, Masahito
AU - Taniguchi, Ryuji
AU - Takai, Kazuhiko
N1 - Funding Information:
This work was financially supported by a Grant-in-Aid for Scientific Research (Nos. 18H03911 and 19H02719) from MEXT, Japan.
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/5/15
Y1 - 2020/5/15
N2 - Treatment of 1,n-enynes with gem-dichromiomethane species prepared in situ from 1,1-diiodomethanes and CrCl2 gave alkenylbicycloalkanes. Alkenylcarbene species, which was generated via [2 + 2] cycloaddition with a triple bond, were intercepted by intramolecular cyclopropanation of a pendant double bond, and alkene metathesis did not proceed. This is a very rare example of transformation of alkynyl CC with gem-dimetalloalkanes. Silyl- and borylcarbene equivalents generated from gem-(dichromio)silyl- and borylmethanes promoted the coupling and cyclization of enediynes as well as 1,n-enynes.
AB - Treatment of 1,n-enynes with gem-dichromiomethane species prepared in situ from 1,1-diiodomethanes and CrCl2 gave alkenylbicycloalkanes. Alkenylcarbene species, which was generated via [2 + 2] cycloaddition with a triple bond, were intercepted by intramolecular cyclopropanation of a pendant double bond, and alkene metathesis did not proceed. This is a very rare example of transformation of alkynyl CC with gem-dimetalloalkanes. Silyl- and borylcarbene equivalents generated from gem-(dichromio)silyl- and borylmethanes promoted the coupling and cyclization of enediynes as well as 1,n-enynes.
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U2 - 10.1021/acs.orglett.0c01304
DO - 10.1021/acs.orglett.0c01304
M3 - Article
C2 - 32324419
AN - SCOPUS:85084719042
SN - 1523-7060
VL - 22
SP - 3985
EP - 3988
JO - Organic Letters
JF - Organic Letters
IS - 10
ER -