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Borane Reduction of the Steroid 20-Ketone Group in the Presence of Various Chiral β-Amino Alcohols (1993)

Göndös, György ; Orr, James C.

Weinheim : Wiley-Blackwell

Liebigs Annalen 1993 (1993), S. 581-582

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ISSN: 0170-2041

Keywords: 5β-Pregnane, 3α-hydroxy-20-one ; Chiral borane reduction ; Borane reduction ; Steroids ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: The direction of reduction of 20-carbonyl group of 3α-hydroxy-5β-pregnan-20-one (1) with a complex of borane-methyl sulfide and chiral β-amino alcohols, depends on the chirality of the amino alcohol. Where there is a 2-phenyl or 2-benzyl substituent, then the S enantiomer gives exclusively the steroid 20R alcohol 3. The R enantiomer of 2-amino-2-phenyl-1-ethanol gives the highest steroid 20S (2):20R (3) alcohol ratio.

Additional Material: 1 Tab.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199319930194

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