Domino Sequences Involving Stereoselective Hydrazone-Type Heck Reaction and Denitrogenative [1,5]-Sigmatropic Rearrangement
Shuling Yu, Lijin Zhou, Sihan Ye and Xiaofeng Tong*
*School of Pharmaceutical and Chemical Engineering & Institute for Advanced Studies, Taizhou University, Taizhou, Zhejiang
318000, China, Email: xftong
tzc.edu.cn
S. Yu, L. Zhou, S. Ye, X. Tong, J. Am. Chem. Soc., 2023, 145, 7621-7627.
DOI: 10.1021/jacs.3c01075
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Abstract
Acid-promoted condensations of N-[(Z)-3-iodoallyl]-aminoacetaldehydes and hydrazine hydrate followed by Pd-catalyzed asymmetric intramolecular hydrazone-type Heck reactions provide allylic diazenes that rapidly undergo stereospecific denitrogenative [1,5]-sigmatropic rearrangement, furnishing 3-substituted tetrahydropyridines with high enantioselectivity.
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proposed mechanism
Key Words
Heck reaction, 1,2,3,6-tetrahydropyridines
ID: J48-Y2023
