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High Syn Selectivity of a S E ′ Reaction: Acylation of an Optically Active 1,1‐Disilyl‐2‐alkene. Preliminary communication
Author(s) -
Wetter Hansjürg,
Scherer Paul,
Schweizer W. Bernd
Publication year - 1979
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.19790620628
Subject(s) - chemistry , absolute configuration , optically active , acylation , reagent , derivative (finance) , enantiomer , ketone , active site , alkylation , alkene , enantiomeric excess , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , financial economics , economics
The disilane/disilylmethane rearrangement of an optically active disilanyl sulfide 9B was used to prepare an optically active disilylalkene 10 whose absolute configuration was established by X‐ray analysis of the bromo derivative 13 ( P 2 1 , a = 7.847 (3) Å, b = 9.487 (3) Å, c = 20.010 (8) Å, β = 82.28° (3), Z = 2). Acylation of 10 furnished an optically active ketone 14 , which was degraded to 16 , a compound of known absolute configuration. The enantiomeric excess of 10 was determined by alkylation with an optically active lithium compound and that of 14 by an optically active NMR.‐shift reagent. The S E ′ reaction 10 → 14 was thus shown to proceed with 94% (97% syn /3% anti ) stereoselectivity.