Metal-Free Cycloetherification by in Situ Generated P-Stereogenic α-Diazanium Intermediates: A Convergent Synthesis of Enantiomerically Pure Dihydrobenzooxaphospholes.
A metal-free tandem reaction, initiated by the generation of a diazonium cation and followed by cycloetherification, was developed. Acid-promoted de-tert-butylation of N-nitroso N-tert-butylamine was used to generate a diazonium cation in situ, demonstrating a new application of nitroso chemistry. This reaction was employed in the synthesis of substituted benzofuran-3(2H)-ones and dihydrobenzo[d][1,3]oxaphosphole 3-oxides.
Shi-Guang
SG
Li
Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
Zhengxu S
ZS
Han
Peter
P
Viereck
Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
Heewon
H
Lee
Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
Dmitry
D
Kurouski
Chemical Development, Boehringer-Ingelheim Pharmaceuticals, Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
Chris H
CH
Senanayake
Youla S
0000-0002-6231-7498
YS
Tsantrizos