Highly stereoselective nucleophilic addition to cyclopropyl carbonyls: The facial selectivity in the cyclopropyl ketones is opposite to that in the corresponding aldehyde

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 221-224

  Ono, Shizuka ^a   Shuto, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0030053286     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02133-7     Document Type: Article

References (30)

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22. The stereochemisty of 5a was confirmed from the X-ray crystallograhic analysis of the O-piodobenzoyl derivative of 5a.
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24. A total of 1174 independent reflections were collected and used for the structure analysis. The final R value was 0.056.
25. The reaction would not proceed via a chelation-controlled pathway, because the stereoselectivity was not changed when the reaction was done in the presence of HMPA (3 mol eq.).
26. Inversion of the configuration of the secondary hydroxyl by nucleophilic substitution reactions was unsuccessful.
27. The target CRA 2a,b and 3a,b were synthesized from 5a,b and 6a,b, respectively.
28. 1H NMR spectrum of the crude product.
29. A total of 1463 independent reflections were collected and used for the structure analysis. The final R value was 0.059.
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