Asymmetric conjugate addition of alkynylboronates to enones [11]

Journal of the American Chemical Society

Volumn 122, Issue 8, 2000, Pages 1822-1823

  Chong, J Michael ^a   Shen, Lixin ^a   Taylor, Nicholas J ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; BORONIC ACID DERIVATIVE; KETONE DERIVATIVE; LITHIUM DERIVATIVE; NAPHTHOL DERIVATIVE;

CHIRALITY; CONJUGATE; ENANTIOMER; ESTERIFICATION; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034054973     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992922b     Document Type: Letter

References (35)

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5. Organozincs: Alexakis, A.; Vastra, J.; Burton, J.; Benhaim, C.; Mangeney, P. Tetrahedron Lett. 1998, 39, 7869-7872 and references therein.
6. It has recently been shown that alkynylcuprates will add to enones in the presence of trialkylsilyl triflates or TMSI: (a) Kim, S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783-786. (b) Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182-187.
7. It has recently been shown that alkynylcuprates will add to enones in the presence of trialkylsilyl triflates or TMSI: (a) Kim, S.; Park, J. H.; Jon, S. Y. Bull. Korean Chem. Soc. 1995, 16, 783-786. (b) Eriksson, M.; Iliefski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182-187.
8. Hudrlik, P. F.; Hudrlik, A. M. Applications of Acetylenes in Organic Synthesis. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; John Wiley and Sons: Chichester, 1978; Part 1, pp 199-273.
9. An account of preliminary work was presented at the 81st Canadian Society for Chemistry Conference and Exhibition, Whistler, BC, Canada, May 31-June 4, 1998, abstract No. 297.
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17. Asymmetric conjugate addition of aryl- and alkenylboronic acids has been described: Takaya, Y.; Ogasawara, M.; Hayashi, T.; Sakai, M.; Miyaura, N. J. Am. Chem. Soc. 1998, 120, 5579-5580.
18. Alkynylboranes have been used in asymmetric alkynylations of aldehydes: Corey, E. J.; Cimprich, K. A. J. Am. Chem. Soc. 1994, 116, 3151.
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23. 2BOR have been used to prepare alkynylboronates: (a) Brown, H. C.; Bhat, N. G.; Srebnik, M. Tetrahedron Lett. 1988, 29, 2631-2634. (b) Deloux, L.; Srebnik, M. J. Org. Chem. 1994, 59, 6871-6873.
24. 2BOR have been used to prepare alkynylboronates: (a) Brown, H. C.; Bhat, N. G.; Srebnik, M. Tetrahedron Lett. 1988, 29, 2631-2634. (b) Deloux, L.; Srebnik, M. J. Org. Chem. 1994, 59, 6871-6873.
25. It has been suggested that reaction of binaphthol with triphenylborate generates the "expected" mixed borate but it has not been isolated or spectrocopically characterized: refs 13b and 13c.
26. Many attempts to prepare mixed alkyl binaphthyl borates gave a boron bridged trimer of binaphthol: Kaufmann, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 545-546.
27. 6) spectra: 4a, δ 3.98; 5a, δ 4.41.
28. 13C NMR spectra consistent with 2a but containing signals for other related compounds as well. The intensities of these other signals increased with time, suggesting slow decomposition of boronate 2a.
29. Addition of substituents in the 3,3′-positions of binaphthol can dramatically increase enantioselectivities: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510-3512. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310- 312. (c) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930.
30. Addition of substituents in the 3,3′-positions of binaphthol can dramatically increase enantioselectivities: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510-3512. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312. (c) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930.
31. Addition of substituents in the 3,3′-positions of binaphthol can dramatically increase enantioselectivities: (a) Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510-3512. (b) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310- 312. (c) Ishihara, K.; Kurihara, H.; Matsumoto, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 6920-6930.
32. When 2b was allowed to react with Z-6a and Z-6d, 7a and 7d were produced in 90% and 4% ee, respectively. In both cases, the major isomer was the same as that produced using the E enone, suggesting isomerization to the E isomer occurred under the reaction conditions.
33. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709-6716.
34. The absolute configurations of the other adducts in Table I are unknown at this time, but it is expected that they will also be consistent with our working model.
35. 4-Cl (2 mL) and water (2 mL) were added to quench the reaction. Standard aqueous workup afforded the 1,4-addition product (see Table 1 for yields) and 3b (>95% recovery).