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Alkylierung in der 2-Stellung von (2S, 4R)- 4-Hydroxyprolin unter Retention (1985)

Weber, Theodor ; Seebach, Dieter

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 68 (1985), S. 155-161

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: Alkylation in the 2-Position of (2S, 4R)-4-Hydroxyproline with Retention of ConfigurationO-Acetyl-4-hydroxyproline (1b) is condensed with pivalaldehyde to give a single stereoisomer of the 2-(tert-butyl)-4-oxo-3-oxa-1-azabicyclo[3.3.0]oct-7-yl acetate (3). This is converted to the enolates 4 or 5, reactions of which with alkyl halides, aldehydes, and acetone (→6,9,10,11) are diastereoselective (lk-1,3-induction). Cleavage of the corresponding products furnishes the enantiomerically pure 2-deuterio-, 2-methyl-, 2-allyl-, and 2-benzyl-substituted 4-hydroxyprolines 2a-2d.

Additional Material: 2 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19850680119

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