9-Allyl-9-borabicyclo[3.3.1]nonane

Uses

9-Allyl-9-borabicyclo[3.3.1]nonane could be used as an allylating reagent for aldehydes, ketones, acid chlorides, amides, and acid anhydrides; reagent for diastereo- and enantioselective allylation of aldimines; diastereoselective allylation of acetals[1-9].

Synthesis

The Preparative Method of 9-Allyl-9-borabicyclo[3.3.1]nonane: prepared from Allyl Bromide and B-methoxy-9-BBN according to a literature  procedure. Crotyl-9-BBN and 2-methallyl-9-BBN are similarly prepared from the corresponding allylic bromides.

storage

Handling, Storage, and Precautions: the neat liquid is highly flammable and must be stored in the absence  of air and moisture. 9-Allyl-9-borabicyclo[3.3.1]nonane (Allyl-9-BBN) may be kept as a CH2Cl2 or THF solution under N2 atmosphere. Use in a fume hood.

References

1. Kramer, G. W.; Brown, H. C. JOM 1977, 132, 9. 2. Kramer, G. W.; Brown, H. C. JOC 1977, 42, 2292. 3. Yamamoto, Y.; Komatsu, T.; Maruyama, K. JOM 1985, 285, 31. 4. Vara Prasad, J. V. N.; Rich, D. H. TL 1990, 31, 1803. 5. Yamamoto, Y.; Komatsu, T.; Maruyama, K. JACS 1984, 106, 5031. 6. Yamamoto, Y.; Nishii, S.; Maruyama, K.; Komatsu, T.; Ito, W. JACS 1986, 108, 7778. 7. Yamamoto, Y.; Ito, W.; Maruyama, K. CC 1985, 1131. 8. Yamamoto, Y.; Komatsu, T.; Maruyama, K. CC 1985, 814. 9. Yamamoto, Y.; Nishii, S.; Yamada, J. JACS 1986, 108, 7116.