Borabicyclo[3.3.2]decanes and the stereoselective asymmetric synthesis of 1,3-diol stereotriads from 1,3-diborylpropenes

Journal of the American Chemical Society

Volumn 131, Issue 3, 2009, Pages 1269-1273

  González, Ana Z ^a   Román, José G ^a   Alicea, Eyleen ^a   Canales, Eda ^a   Soderquist, John A ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALDIMINES; ALLYLATION; ALLYLBORATION; AMINO ALCOHOLS; DIASTEREOMERS; KETIMINES; MOLECULAR GATES; REGIOISOMERS; SHUT DOWN; STEREOGENIC CENTERS; STEREOSELECTIVE ASYMMETRIC SYNTHESIS; THERMODYNAMIC MIXTURES;

ALCOHOLS; ALDEHYDES; AMINES; KETONES;

SYNTHESIS (CHEMICAL);

1,3 DIBORYLPROPENE; ALDEHYDE; ALLYL COMPOUND; BORIC ACID; DECANE; IMINE; KETONE DERIVATIVE; PROPYLENE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 67749114480     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808360z     Document Type: Article

References (23)

1. For the synthesis of anti-1,2-diols see: (a) Roush, W. R.; Grover, P. T. Tetrahedron 1992, 48, 1981.
2. (b) Roush, W. R.; Grover, P. T. Tetrahedron Lett. 1990, 31, 7567.
3. Hunt, J. A.; Roush, W. R. J. Org. Chem. 1997, 62, 1112.
4. Barrett, A. G. M.; Malecha, J. W. J. Org. Chem. 1991, 56, 5243.
5. (e) Brown, H. C.; Narla, G. J. Org. Chem. 1995, 60, 4686.
6. For bimetallic double-allylating reagents, see: (a) Roush, W. R.; Pinchuk, A. N.; Micalizio, G. C. Tetrahedron Lett. 2000, 41, 9413.
7. (b) Flamme, E. M.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 13644.
8. Flamme, E. M.; Roush, W. R. Org. Lett. 2005, 7, 1411.
9. Barrett, A. G. M.; Braddock, D. C.; de Koning, P. D.; White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65, 375.
10. (e) Peng, F.; Hall, D. G. J. Am. Chem. Soc. 2007, 129, 3070, and references cited therein.
11. (a) Burgos, C.; Canales, E.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 8044.
12. (b) Canales, E.; Prasad, K. G.; Soderquist, J. A. J. Am. Chem. Soc. 2005, 127, 11572.
13. Hernandez, E.; Canales, E.; Gonzalez, E.; Soderquist, J. A. Pure Avvl. Chem. 2006, 78, 1389.
14. Canales, E.; Hernandez, E.; Soderquist, J. A. J. Am. Chem. Soc. 2006, 128, 8712. Hernandez, E.; Burgos, C. H.; Alicea, E.; Soderquist, J. A. Org. Lett. 2006, 8, 4089.
15. (e) Lai, C.; Soderquist, J. A. Org. Lett. 2005, 7, 799.
16. (f) Gonzalez, A. Z.; Roman, J. G.; Gonzalez, E.; Martinez, J.; Medina, J. R.; Matos, K.; Soderquist, J. A. J. Am. Chem. Soc. 2008, 130, 9218.
17. In the notation for trans-1SR and all related compounds, the first letter gives the stereochemical assignment of the 10-position in the 10-Ph- 9-BBD moiety and the second letter that in the 10-TMS-9-BBD moiety [e.g., trans-1SR contains (S)-10-Ph-9-BBD and (R)-10-TMS-9-BBD moieties].
18. Although trans-2 could result from the hydroboration of the B- propargyl isomer of 3 with 4, we felt that a cis → trans isomerization pathway offered a more plausible explanation for these hydroboration products since it was already implicated in the formation of trans-1.
19. The magnitude of this coupling constant is in complete agreement with those of other cs-vinylborane species. See: Soderquist, J. A.; Rane, A. M.; Matos, K.; Ramos, J. Tetrahedron Lett. 1995, 36, 6847.
20. (a) Canales, E.; Gonzalez, A. Z.; Soderquist, J. A. Angew Chem., Inti Ed. 2007, 46, 397.
21. (b) Gonzalez, A. Z.; Soderquist, J. A. Org. Lett. 2007, 9, 1081.
22. Fang, G. Y.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2007, 46, 359.
23. Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano, S. J. Chem. Soc., Perkin Trans. 1 200l, 645.