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An Unexpected Asymmetric Reduction of 4‐(1‐Nitro‐2‐oxocyclododecyl)butan‐2‐one. Determination of the absolute configuration of (‒)‐15‐hexadecanolide
Author(s) -
Stanchev Stephan,
Hesse Manfred
Publication year - 1989
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19890720523
Subject(s) - chemistry , absolute configuration , nitro , hydride , reduction (mathematics) , enantiomer , stereochemistry , medicinal chemistry , hydrogen , organic chemistry , alkyl , geometry , mathematics
Reduction of the carbonyl group in the side chain of 4‐(1‐nitro‐2‐oxocyclododecyl)butan‐2‐one ( 3 ) with organoboron complexes are influenced by the chiral center, in 4‐position with respect to the carbonyl C‐atom, to which the NO 2 group is attached, a rare type for an asymmetric reduction. Independent of the ( R )‐ or ( S )‐configuration of the Alpine ‐ Hydride , (+)‐ 3 is reduced only to the (15 S )‐nitrolactone (+)‐ 5 and, after subsequent transformations, to (+)‐(‐ S )‐15‐hexadecanolide ((+)‐ 1 ), enantiomer of the naturally occurring (−)‐ 1 .