TY - JOUR

T1 - Chemo- and Diastereoselective Entries into All-Carbon α-Quaternary Aldehydes via C–C Insertion of 4-Diazoisoquinolin-3-ones into C–CHO Bonds

AU - Левашова, Екатерина Юрьевна

AU - Адамчик, Мария Александровна

AU - Кантин, Григорий Павлович

AU - Дарьин, Дмитрий Викторович

PY - 2023/7/26

Y1 - 2023/7/26

N2 - Herein, we describe a chemo- and diastereoselective formal C-C insertion reaction of 1,2-disubstituted 4-diazo-3(2H)-isoquinolones and 4-diazoisochroman-3-one into C-CHO bonds of aldehydes, delivering all-carbon α-quaternary aldehydes bearing medicinally important 1,4-dihydro-3(2H)-isoquinolone scaffold. Our protocol is enabled by the preferential 1,2-carbon migration over more common 1,2-H shift. The corresponding reaction tolerates a wide range of functionalities in both aldehyde and diazo components, giving the target homologated aldehydes in generally high yields. The synthetic utility of this method has been further showcased by some transformations of the formyl moiety.

AB - Herein, we describe a chemo- and diastereoselective formal C-C insertion reaction of 1,2-disubstituted 4-diazo-3(2H)-isoquinolones and 4-diazoisochroman-3-one into C-CHO bonds of aldehydes, delivering all-carbon α-quaternary aldehydes bearing medicinally important 1,4-dihydro-3(2H)-isoquinolone scaffold. Our protocol is enabled by the preferential 1,2-carbon migration over more common 1,2-H shift. The corresponding reaction tolerates a wide range of functionalities in both aldehyde and diazo components, giving the target homologated aldehydes in generally high yields. The synthetic utility of this method has been further showcased by some transformations of the formyl moiety.

UR - https://www.mendeley.com/catalogue/6499760f-8de3-3594-aba7-90c575f3f7d4/

U2 - 10.1021/acs.joc.3c01222

DO - 10.1021/acs.joc.3c01222

M3 - Article

VL - 88

SP - 11217

EP - 11226

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 15

ER -