Formation of optically pure cyclic amines by intramolecular conjugate displacement

DOI: 10.1021/jo3001657

Source and publish data:

Journal of Organic Chemistry p. 3348 - 3364 (2012)

Update date:2022-08-04

Topics:

Authors:

Cheng, Ping

Clive, Derrick L. J.

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Article abstract of DOI:10.1021/jo3001657

Intramolecular conjugate displacement (ICD) has been applied to the Morita-Baylis-Hillman adducts formed from (5S)-5-(l-menthyloxy)-2(5H)-furanone and aldehydes that carry a protected β- or γ-amino group. DIBAL-H reduction of the resulting ICD products releases optically pure six- or seven-membered cyclic amines having a stereogenic center α to nitrogen.

Full text of DOI:10.1021/jo3001657

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