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Enantioselective Desymmetrization of Tropinone Derivatives by Hydroboration

Year: 2003

Type: article

Abstract: N-Protected tropenone derivs. I (R = CO2Me, CBZ, Ts) prepd. from the resp. pyrroles and tetrabromoacetone, were used as starting materials for desymmetrization by hydroboration of the C-C double bond. Hydroboration of I with (-)-(Ipc)2BH followed by oxidn., however, gave the desired 6-hydroxylated product only in low yield due to byproduct formation. After acetalization of the carbonyl group in I, the corresponding acetals were desymmetrized with (Ipc)2BH and oxidative workup to chiral alcs. II in good yields with excellent enantiomeric excesses in most cases.

Source: Synlett

DOI: 10.1055/s-2003-42080

Authors: Sabine Laschat, Nicolai Cramer, Angelika Baro, Wolfgang Frey

Institution: University of Stuttgart

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: Deutsche Forschungsgemeinschaft

OpenAlex ID: W2086122780

FWCI:

Cites:

Cited by: 4

Related to: 10