Parallel Differentiated Recognition of Ketones and Acetals

Angewandte Chemie - International Edition

Volumn 37, Issue 1-2, 1998, Pages 91-93

  Chen, Jian Xie ^a   Otera, Junzo ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Aldol reactions carbony1 differentiation; Chemoselectivity; One pot reactions; tin

Indexed keywords

EID: 0031881550     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980202)37:1/2<91::aid-anie91>3.0.co;2-a     Document Type: Article

References (24)

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7. Mori et al. reported the analogous differentiation between aldehydes, but not different functional groups, by kelene silyl acetal and trimethylsilyl cyanide: A. Mori, H. Ohno, S. Inoue, Chem. Lett. 1992, 631. Parallel kinetic resolution would be another relevant reaction if enantiomers are regarded as different substrates: J. Brandt, C. Jochum, I. Ugi, Tetrahedron, 1977, 33, 1353; E. Vedejs, X. Chen, J. Am. Chem. Soc. 1997, 119, 2584.
8. Mori et al. reported the analogous differentiation between aldehydes, but not different functional groups, by kelene silyl acetal and trimethylsilyl cyanide: A. Mori, H. Ohno, S. Inoue, Chem. Lett. 1992, 631. Parallel kinetic resolution would be another relevant reaction if enantiomers are regarded as different substrates: J. Brandt, C. Jochum, I. Ugi, Tetrahedron, 1977, 33, 1353; E. Vedejs, X. Chen, J. Am. Chem. Soc. 1997, 119, 2584.
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10. 2, -78°C,2h; yield of isolated product: 91%.
11. 2, -78°C, 5 h; yield of isolated product: 63%.
12. 2, -78°C, 5 h. It is crucial to use an excess of 2 to consume 4 as quickly as possible, otherwise the decomposition of the catalyst is inevitable during the reaction, resulting in low yields of 7.
13. 2, -78°C, 7 h. Yields of isolated products were determined after column chromatography.
14. 3CN).
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23. Chemical shifts of the diastereomer are given in the parentheses.
24. It is conceivable that there are diasteromers, yet no NMR evidence was obtained explicitly.