Bidentate organoaluminum Lewis acid for selective activation of carbonyl over acetal functionality: Chemoselective functionalization

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7403-7406

  Takashi, Ooi ^a   Tayama, Eiji ^a   Takahashi, Makoto ^a   Maruoka, Keiji ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0342683877     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01735-8     Document Type: Article

References (16)

1. Recent reviews of molecular recognition: (a) D'Souza, V. T.; Bender, M. L. Acc. Chem. Res. 1987, 20, 146.
2. (b) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245.
3. (c) Rebek, J., Jr. Acc. Chem. Res. 1990, 23, 399.
4. Sato, T.; Otera, J.; Nozaki, H. J. Org. Chem. 1993, 55, 4971, and references cited therein.
5. (a) Mori, A.; Maruoka, K.; Yamamoto, H. Tetrahedron Lett. 1984, 25, 4421.
6. (b) Murata, S.; Suzuki, M.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 3248.
7. (c) Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 37, 3899.
8. Otera, J.; Chen, J. Synlett 1996, 321. See also: Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901.; Mukaiyama, T.; Ohno, T,; Han, J. S.; Kobayashi, S. Chem. Lett. 1991, 949.
9. Otera, J.; Chen, J. Synlett 1996, 321. See also: Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901.; Mukaiyama, T.; Ohno, T,; Han, J. S.; Kobayashi, S. Chem. Lett. 1991, 949.
10. Otera, J.; Chen, J. Synlett 1996, 321. See also: Sato, T.; Otera, J.; Nozaki, H. J. Am. Chem. Soc. 1990, 112, 901.; Mukaiyama, T.; Ohno, T,; Han, J. S.; Kobayashi, S. Chem. Lett. 1991, 949.
11. Ooi, T.; Takahashi, M.; Maruoka, K. J. Am. Chem. Soc. 1996, 118, 11307.
12. For reviews of the Mukaiyama aldol reaction, see: (a) Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1977, 16, 817.
13. (b) Mukaiyama, T. Org. React. 1982, 1043. See also: Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043.
14. (b) Mukaiyama, T. Org. React. 1982, 1043. See also: Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043.
15. 3 by 1 was attempted at -78 °C to evaluate intrinsic reactivity of the acetal itself, which resulted in the formation of aldol product in 37% yield (cf. entries 1 and 2 in Table 1). Therefore, the high chemoselectivity observed herein is ascribed to the rate difference between the aldol reaction of carbonyl compounds and that of their corresponding acetals based on the double electrophilic activation of carbonyls.
16. Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.