Formation of transient chiral allenylindium reagents from enantioenriched propargylic mesylates through oxidative transmetalation. Applications to the synthesis of enantioenriched homopropargylic alcohols

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 696-697

  Marshall, James A ^a   Grant, Charsetta M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MESYLIC ACID DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ORGANIC CHEMISTRY; OXIDATION; STRUCTURE ANALYSIS;

EID: 0033524869     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982255p     Document Type: Article

References (25)

1. Yamamoto, H. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.3.
2. Marshall, J. A. Chem. Rev. 1996, 96, 31.
3. Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1997, 62, 6001. Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. Marshall, J. A.; Johns, B. A.; J. Org. Chem. 1998, 63.
4. Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1997, 62, 6001. Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. Marshall, J. A.; Johns, B. A.; J. Org. Chem. 1998, 63.
5. Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1997, 62, 6001. Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. Marshall, J. A.; Johns, B. A.; J. Org. Chem. 1998, 63.
6. Cf. Marshall, J. A.; Perkins, J. F.; Wolf, M. A.; J. Org. Chem. 1995, 60, 5556.
7. Marshall, J. A.; Chemtracts - Organic Chemistry 1997, 10, 481.
8. Elsevier: C. J.; Vermeer, P.; Gedanken, A.; Runge, W. J. Org. Chem. 1985, 50, 364.
9. DMA = N,N-dimethylacetamide, DMPU = N,N-dimethylpropylene-urea, DPS = diphenyl-tert-butylsilyl.
10. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812. Tamaru, Y.; Goto, S.; Tanaka, A.; Shimizu, M.; Kimura, M. Angew Chem., Int. Ed. Engl. 1996, 35, 878.
11. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812. Tamaru, Y.; Goto, S.; Tanaka, A.; Shimizu, M.; Kimura, M. Angew Chem., Int. Ed. Engl. 1996, 35, 878.
12. 2-OAc to undergo 1,2- as opposed to 1,4-additions to conjugated aldehydes and ketones. Trost, B. M.; Sharma, S.; Schmidt, T. J. Am. Chem. Soc. 1992, 114, 7903.
13. 2], InI, and the alcohol precursor of mesylate 1 are available from the Aldrich Chemical Co., Milwaukee, WI.
14. 3P analogue was first examined in our laboratory by N. D. Adams.
15. The stereochemistry of the adducts was established by comparison to authentic samples. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1997, 62, 8976.
16. Roush, W. R.; Palkowitz, A. D.; Palmer, M. A. J. Org. Chem. 1987, 52, 316.
17. The structure of these adducts is assigned by comparison with authentic samples prepared from aldehydes 7 and ent-7 by N. D. Adams as described in ref 12.
18. 2. Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 2275. Aurrecoechea, J. M.; Fañanás-San Antón, R. J. Org. Chem. 1994, 59, 702.
19. 2. Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Chem. Lett. 1987, 2275. Aurrecoechea, J. M.; Fañanás-San Antón, R. J. Org. Chem. 1994, 59, 702.
20. Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577. Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1996. Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215.
21. Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577. Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1996. Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215.
22. Takahara, J. P.; Masuyama, Y.; Kurusu, Y. J. Am. Chem. Soc. 1992, 114, 2577. Matsubara, S.; Wakamatsu, K.; Morizawa, Y.; Tsuboniwa, N.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1985, 58, 1996. Tabuchi, T.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 215.
23. Trost, B. M.; Herndon, J. W. J. Am. Chem. Soc. 1984, 106, 6835.
24. Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3702. Zhang, P.; Zhang, W.; Zhang, T.; Wang, Z.; Zhore, W. J. Chem. Soc., Chem. Commun. 1991, 491.
25. Masuyama, Y.; Kinugawa, N.; Kurusu, Y. J. Org. Chem. 1987, 52, 3702. Zhang, P.; Zhang, W.; Zhang, T.; Wang, Z.; Zhore, W. J. Chem. Soc., Chem. Commun. 1991, 491.