Alkoxy-directed radical reductions of ketones using trichlorosilane

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2610-2611

  Enholm, Eric J ^a   Schulte II, James P ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXANONE DERIVATIVE; KETONE DERIVATIVE; RADICAL; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0033574388     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981763w     Document Type: Article

References (21)

1. For a review, see: Cary, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum Press: New York, 1990; Part B, p 232-244.
2. Pereyre, M.; Quintard, J. P.; Rahm A. Tin in Organic Synthesis; Butterworths: Boston, 1987.
3. Molander, G. A. Chem. Rev. 1992, 92, 29-68.
4. (a) Alberti, A.; Chatgilialoglu, C. Tetrahedron 1990, 46, 3963-3972.
5. (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194.
6. (c) Kulicke, K. J.; Giese, B. Synlett 1990, 91-92.
7. (d) Giese, B. Damm, W.; Dickhaut, J.; Wetterich, F.; Sun, S.; Curran, D. P. Tetrahedron Lett. 1991, 32, 6097-6100.
8. For a review, see: Smith, M. B. Organic Synthesis; McGraw-Hill: New York, 1994; p 403.
9. 3SiH, see: Kraus, G. A.; Liras, S. Tetrahedron Lett. 1990, 31, 5265-5268.
10. Crich, D.; Sun S. J. Org. Chem. 1996, 61, 7200-7201 and references therein.
11. Sun, D. H.; Bent, B. E.; Wright, A. P.; Naasz, B. M. J. Mol. Catal. 1998, 131, 169-83.
12. 3SnH for $71.70.
13. (a) Sano, H.; Takeda, T.; Migita, T. Chem. Lett. 1988, 119-122.
14. (b) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. Cs. Tetrahedron Lett. 1992, 33, 6629-6632.
15. (c) Giese, B.; Kopping, B. Tetrahedron Lett. 1989, 30, 681-684.
16. Ketone 7a was prepared by the reaction of cyclohexanecarboxaldehyde with the Grignard reagent of α-bromostyrene in THF at 0 °C. Ozonolysis of the product in dichloromethane at -78 °C, followed by dimethyl sulfide quench, gave 7a in 85% yield for the two-step synthetic sequence.
17. Nakata, T.; Tanaka, T.; Oishi, T. Tetrahedron Lett. 1983, 24, 2653-2656.
18. For a similar mechanistic analysis using TTMSS, see ref 4c.
19. (a) Allen, A. D.; Charlton, J. C.; Eaborn, C.; Modena, G. J. Chem. Soc. 1957, 3668-3670.
20. (b) Allen, A. D.; Modena, G. J. Chem. Soc. 1957, 3671-3678.
21. Havill, M. E.; Joffe, I.; Post, H. W. J. Org. Chem. 1948, 13, 280-283.