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Synfacts 2023; 19(07): 0669
DOI: 10.1055/s-0042-1752577
Metals in Synthesis

An Asymmetric Intramolecular Heck-Type Reaction of in situ Generated Hydrazones

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Phillip Pommerening
Yu S, Zhou L, Ye S, Tong X. * Taizhou University, Zhejiang, P. R. of China
Domino Sequences Involving Stereoselective Hydrazone-Type Heck Reaction and Denitrogenative [1,5]-Sigmatropic Rearrangement.

J. Am. Chem. Soc. 2023;
145: 7621-7627
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Key words

Heck-type reaction - hydrazones - palladium catalysis - [1,5]-sigmatropic rearrangement - tetrahydropyridines

Significance

Tong and co-workers have disclosed a domino sequence of a hydrazone-type Heck reaction followed by a stereospecific denitrogenative [1,5]-sigmatropic rearrangement to access 3-substituted tetrahydropyridines in good yields and excellent enantioselectivities.


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Comment

Using chiral substrates derived from amino alcohols, high diastereoselectivities were obtained using DPPB [1,4-bis(diphenylphosphino)-butane] as the ligand (see dashed box). Mechanistic studies such as deuterium-labeling experiments support the shown mechanism.


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Publication History

Article published online:
16 June 2023

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