Unprecedented Preference for Aldehyde over Acetal in Organotin Lewis Acid-Promoted Mukaiyama-Aldol Reaction of Ketene Silyl Acetals

Synlett

Volumn 1996, Issue 4, 1996, Pages 321-323

  Otera, Junzo ^a   Chen, Jianxie ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

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Indexed keywords

EID: 0343191435     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5433     Document Type: Article

References (12)

1. Mukaiyama, T. Angew. Chem. Int. Ed. Engl. 1977, 16, 817. Mukaiyama, T. Org. React. 1982, 28, 203.
2. Mukaiyama, T. Angew. Chem. Int. Ed. Engl. 1977, 16, 817. Mukaiyama, T. Org. React. 1982, 28, 203.
3. Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043.
4. For differentiations between carbonyls and acetals, see Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1993, 58, 4971, and references cited therein.
5. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.
6. Mori, A.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1984, 25, 4421.
7. Nozaki, H.; Otera, J.; Sato, T. J. Synth. Org. Chem. Jpn. 1989, 47, 90. Otera, J. In "Advances in Detailed Reaction Mechanisms", Coxon, J. M. Ed.; JAI Press Inc., 1994, Vol. 3, p167.
8. Nozaki, H.; Otera, J.; Sato, T. J. Synth. Org. Chem. Jpn. 1989, 47, 90. Otera, J. In "Advances in Detailed Reaction Mechanisms", Coxon, J. M. Ed.; JAI Press Inc., 1994, Vol. 3, p167.
9. Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901.
10. 2 at room temperature for 2 h. The resulting solution was in situ employed as a catalyst solution.
11. For preparation of DBTT, see ref. 7. DBTT is also commercially available from Tokyo Chemical Industry Co., Ltd.
12. We have confirmed that the same selectivity holds with benzaldehyde derivatives as well.