Convenient synthesis of enantiomerically enriched (oxybutenyl)stannanes and their Lewis acid catalyzed homoaldol reactions

Synthesis

Volumn , Issue 1, 1996, Pages 141-144

  Paulsen, Holger ^a   Graeve, Claudia ^a   Hoppe, Dieter ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

( ) sparteine induced lithiation; 1,3 chirality transer; allyl carbamates; enantioenriched allylstannanes; enantioselective homoaldol reaction

Indexed keywords

ORGANOTIN COMPOUND;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030040452     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4172     Document Type: Article

References (43)

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29. E′ tin-titanium exchange the same intermediate will result. We concluded this from the fact that the ee values of the corresponding homoaldol products are independent from the presence of this stereoisomer.
30. The product holds approximately 3% of the (2Z)-isomer of unknown configuration. It presumably arises from a contamination of the (E)-crotyl carbamate by approx. 3% of (Z)-5.
31. For further examples see: Paulsen, H., Graeve, C.; Fröhlich, R.; Hoppe, D. Synthesis, 1996, 145.
32. (R)-8a was stored for 2 months at 0°C in the dark without decomposition or racernization.
33. Hoppe, D.; Tarara, G.; Wilckens, M. Synthesis 1989, 83.
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