Manganese η2-complexes as auxiliaries for stereoselective aldol synthesis of allenyl carbinols

Organic Letters

Volumn 12, Issue 21, 2010, Pages 5078-5080

  Bhowmick, Manishabrata ^a   Lepore, Salvatore D ^a  

^a FLORIDA ATLANTIC UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; ALKADIENE; ALLENE; MANGANESE; METHANOL;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; ALKADIENES; CRYSTALLOGRAPHY, X-RAY; MANGANESE; METHANOL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 78049495804     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1021096     Document Type: Article

References (27)

1. Cheng, B.; Liebeskind, L. S. Org. Lett. 2009, 11, 3682
2. Coombs, T. C.; Zhang, Y.; Garnier-Amblard, E. C.; Liebeskind, L. S. J. Am. Chem. Soc. 2009, 131, 876
3. Zhang, Y.; Liebeskind, L. S. J. Am. Chem. Soc. 2005, 127, 11258
4. For recent examples, see
5. Shi, M.; Tang, X.-Y.; Yang, Y.-H. J. Org. Chem. 2008, 73, 5311
6. Huang, X.; Shen, R.; Zhang, T. J. Org. Chem. 2007, 72, 1534
7. Hopkins, C. D.; Guan, L.; Malinakova, H. C. J. Org. Chem. 2005, 70, 6848
8. Ma, S. Chem. Rev. 2005, 105, 2829
9. Maity, P.; Lepore, S. D. J. Am. Chem. Soc. 2009, 131, 4196
10. Xu, B.; Hammond, G. B. Angew. Chem., Int. Ed. 2008, 47, 689
11. Miesch, L.; Welsch, T.; Rietsch, V.; Miesch, M. Chem.-Eur. J. 2009, 15, 4394
12. Miesch, L.; Rietsch, V.; Welsch, T.; Miesch, M. Tetrahedron Lett. 2008, 49, 5053
13. Miesch, L.; Welsch, T.; Rietsch, V.; Miesch, M. Chem.-Eur. J. 2009, 15, 4394
14. Miesch, L.; Rietsch, V.; Welsch, T.; Miesch, M. Tetrahedron Lett. 2008, 49, 5053
15. Tsuboi, S.; Kuroda, H.; Takatsuka, S.; Fukawa, T.; Sakai, T.; Utaka, M. J. Org. Chem. 1993, 58, 5952
16. Petasis, N. A.; Teets, K. A. J. Am. Chem. Soc. 1992, 114, 10328
17. Frank-Neumann, M.; Brion, F. Angew. Chem., Int. Ed. 1979, 18, 688
18. Giffard, M.; Gentric, E.; Touchard, D.; Dixneuf, P. J. Organomet. Chem. 1977, 129, 371
19. Giffard, M.; Dixneuf, P. J. Organomet. Chem. 1977, 85, C26
20. Lepore, S. D.; Khoram, A.; Bromfield, D. C.; Cohn, P.; Jairaj, V.; Silvestri, M. A. J. Org. Chem. 2005, 70, 7443
21. Our early studies in this vein revealed that a direct alkylation of an alkynyl ester to give allene product is usually not possible except in the presence of multiple equivalents of strong amide bases leading to dianion intermediates. Even under these forcing conditions, the method was limited to the formation of allenyl esters with α-silyl, stannyl, and methyl substitution
22. Lepore, S. D.; He, Y. J.; Damisse, P. J. Org. Chem. 2004, 69, 9171
23. Lepore, S. D.; He, Y. J. J. Org. Chem. 2005, 70, 4546
24. Our attempts to obtain α-substituted allenyl esters from β-keto esters using an efficient dehydrative protocol also suffered similar limitations
25. Maity, P.; Lepore, S. D. J. Org. Chem. 2009, 74, 158
26. The MMD complexes are air- and light-stable and amenable to flash chromatography. The auxiliary is introduced by replacing a carbon monoxide ligand on methylcyclopentadienyl manganese tricarbonyl (MMT) with the alkynyl ketone or ester substrate. The MMT reagent is inexpensive and widely available (e.g., Bosche Scientific, Inc. for less than $1/g).
27. Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660