Synthesis of enantiopure N-tert-butoxycarbonyl-2-aminocycloalkanones

DOI: 10.1080/00397919208021127

Source and publish data:

Synthetic Communications p. 3003 - 3012 (1992)

Update date:2022-09-26

Topics:

Authors:

Aube Aube

Wolfe Wolfe

Yantiss Yantiss

Cook Cook

Takusagawa

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Article abstract of DOI:10.1080/00397919208021127

A route to enantiomerically pure N-tert-butoxycarbonyl-2-aminocycloalkanones (ring size: 5-8 membered) from the corresponding cycloalkene oxides is described. The procedure involves (1) aminolysis with (S)-α-methylbenzylamine/Me₃Al and chromatographic separation of diastereomers, (2) hydrogenolysis to afford the trans-2-aminocycloalkanols, (3) tert-butoxycarbonyl (Boc) protection, and (4) PCC oxidation.

Full text of DOI:10.1080/00397919208021127

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