Indium trichloride-promoted tin-mediated carbonyl allylation in water: High simple diastereo- and diastereofacial selectivity

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1535-1538

  Li, Xu Ran ^a   Loh, Teck Peng ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALDEHYDE; BROMIDE; INDIUM CHLORIDE; TIN; WATER;

ARTICLE; DIASTEREOISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0029882369     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00174-7     Document Type: Article

References (30)

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27. (c) We have recently found that the reactions proceeded albeit more slowly, with as little as 0.1 equiv. of indium trichloride with respect to tin and allyllic bromide. In contrast to the system reported by Marshall and co-workers (ref. 3a), we have found that premixing of the indium trichloride, allylic bromide and tin increases rate and diastereofacial selectivity of the reaction. We are presently working to determine the fate of the tin species.
28. 1H NMR similarity.
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30. This research was assisted financially by the National University of Singapore (Research Grant No. RP 940633, RP 930657 and 950609).