Asymmetric [2 + 1] cycloaddition reactions of 1-seleno-2-silylethene

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4046-4050

  Yamazaki, Shoko ^a   Tanaka, Mayumi ^a   Yamabe, Shinichi ^a  

^a NARA UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001278988     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960194u     Document Type: Article

References (44)

1. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
2. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
3. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
4. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
5. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
6. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
7. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
8. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
9. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
10. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
11. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
12. For recent examples of asymmetric synthesis of cyclopropanes, see: (a) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M. Y.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, G. H.; Zhou, Q.-L.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763 and references cited therein. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081 and references cited therein. (c) Denmark, S. E.; Christenson, B. L.; Coe, D. M.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2215. Denmark, S. E.; Christensen, B. L.; O'Connor, S. P. Tetrahedron Lett. 1995, 36, 2219. (d) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511. (e) White, J. D. J. Am. Chem. Soc. 1995, 117, 6224. (f) White, J. D.; Kim, T-S.; Mambu, M. J. Am. Chem. Soc. 1995, 117, 5612. (g) Critcher, D. I.; Connolly, S.; Wills, M. Tetrahedron Lett. 1995, 36, 3763. (h) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407. (i) Zhao, Y.; Yang, T.; Lee, M.; Lee, D.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 5236. (J) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393 and references cited therein.
13. (a) Yamazaki, S.; Tanaka, M.; Yamaguchi, A.; Yamabe, S. J. Am. Chem. Soc. 1994, 116, 2356.
14. (b) Yamazaki, S.; Katoh, S.; Yamabe, S. J. Org. Chem. 1992, 57, 4.
15. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
16. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
17. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
18. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
19. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
20. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
21. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
22. Molecular sieves (MS4A) were dried overnight at 250 °C in vacuum or at 350 °C in air before use. The effect of molecular sieves on enantioselectivity in this reaction was not examined. For previous examples of the use of molecular sieves in reactions of chiral titanium alkoxides, see: (a) Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765. (b) Narasaka, K.; Iwasawa, N.; Inoue, M.; Yamada, T.; Nakashima, M.; Sugimori, J. J. Am. Chem. Soc. 1989, 111, 5340. Narasaka, K.; Hayashi, Y.; Shimadzu, H.; Niihata, S. J. Am. Chem. Soc. 1992, 114, 8869. (c) Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1989, 111, 1940. Mikami, K.; Terada, M.; Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949. Mikami, K.; Motoyama, Y.; Terada, M. J. Am. Chem. Soc. 1994, 116, 2812. (d) Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kühnle, F. N. M. J. Org. Chem. 1995, 60, 1788.
23. 4 were measured by weight each time. All results shown in Table 1 were obtained by the latter method.
24. 4 gave 3a in very low chemical yields (5%, 68% ee).
25. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
26. Romo, D.; Romine, J. L.; Midura, W.; Meyers, A. I. Tetrahedron 1990, 46, 4951.
27. Bestmann, H.; Stransky, W.; Vostrowsky, O. Chem. Ber. 1976, 109, 1694.
28. 3) in 3a (for numbering, see eq 2) is determined as (R,R) by 2D-NOESY. See ref 8 in the following paper: Yamazaki, S.; Tanaka, M.; Inoue, T.; Morimoto, N.; Kumagai, H.; Yamamoto, Y. J. Org. Chem. 1995, 60, 6546.
29. 11 gave trans cyclopropane predominantly.
30. Yamazaki, S.; Tanaka, M. Unpublished results.
31. Dijkgraaf, C.; Roussrau, J. P. G. Spectrochim. Acta A 1968, 2, 1213.
32. 2(R-BINOLate) (eq 5)
33. (a) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807, and references cited therein.
34. (b) Watenpaugh, K.; Caughlan, C. N. Inorg. Chem. 1966, 5, 1782.
35. (c) Terada, M.; Mikami, K.; Nakai, T. J. Chem. Soc., Chem. Commun. 1990, 1623.
36. (a) Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Am. Chem. Soc. 1995, 117, 4435.
37. (b) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1995, 60, 6847.
38. See also: (c) Haase, C.; Sarko, C. R.; DiMare, M. J. Org. Chem. 1995, 60, 1777. Reference 3d.
39. 2
40. (a) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270.
41. (b) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284.
42. (c) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
43. (a) Frisch, M. J.; Trucks, G. W.; Head-Gordon, M.; Gill, P. M. W.; Wong, M. W.; Foresman, J. B.; Johnson, B. G.; Schlegel, H. B.; Robb, M. A.; Repologle, E. S.; Gomperts, R.; Andreas, J. L.; Raghavachrni, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92, Revision C; Gaussian, Inc., Pittsburgh, PA, 1992.
44. (b) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.1, Gaussian, Inc., Pittsburgh, PA, 1995. Ab initio calculations using Gaussian 92 and 94 were made on the Convex spp1200/XA at the Information Processing Center (Nara University of Education).