TY - JOUR
T1 - Enantioselective Multicomponent Reaction for Rapid Construction of 1,2,5-Triol Derivatives with Vicinal Chiral Centers
AU - Li, Mingfeng
AU - Guo, Xin
AU - Zheng, Qing
AU - Hu, Wenhao
AU - Liu, Shunying
N1 - Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/5/19
Y1 - 2017/5/19
N2 - 1,2,5-Triol derivatives with vicinal chiral centers have been synthesized from simple starting materials by one-pot method in good yields and with an excellent enantioselectivity. This process was promoted by a chiral secondary amine and iridium(I) cocatalyzed three-component reaction of aryldiazoacetates and alcohols with enals as electrophiles followed by a reduction with NaBH4. Iridium(I)-associated oxonium ylide intermediates were efficiently generated and successfully trapped by the amine-activated enals via a selective 1,4-addition manner, generating enantioselective three-component coupling products.
AB - 1,2,5-Triol derivatives with vicinal chiral centers have been synthesized from simple starting materials by one-pot method in good yields and with an excellent enantioselectivity. This process was promoted by a chiral secondary amine and iridium(I) cocatalyzed three-component reaction of aryldiazoacetates and alcohols with enals as electrophiles followed by a reduction with NaBH4. Iridium(I)-associated oxonium ylide intermediates were efficiently generated and successfully trapped by the amine-activated enals via a selective 1,4-addition manner, generating enantioselective three-component coupling products.
UR - https://www.scopus.com/pages/publications/85019382547
U2 - 10.1021/acs.joc.7b00473
DO - 10.1021/acs.joc.7b00473
M3 - 文章
C2 - 28440635
AN - SCOPUS:85019382547
SN - 0022-3263
VL - 82
SP - 5212
EP - 5221
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 10
ER -