Kinetic resolution of P-stereogenic phosphine boranes via deprotonation using s-butyllithium/(-)-sparteine

Tetrahedron Asymmetry

Volumn 20, Issue 21, 2009, Pages 2432-2434

  Granander, Johan ^a   Secci, Francesco ^a   O'Brien, Peter ^a   Kelly, Brian ^b  

^a UNIVERSITY OF YORK   (United Kingdom)

^b Celtic Catalysts Ltd   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BENZYL BROMIDE; BORANE DERIVATIVE; LITHIUM DERIVATIVE; PHOSPHINE DERIVATIVE; SPARTEINE;

ARTICLE; CHEMICAL REACTION KINETICS; DEPROTONATION; ENANTIOSELECTIVITY; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 72049087460     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.10.026     Document Type: Article

References (16)

1. Crépy K.V.L., and Imamoto T. Adv. Synth. Catal. 345 (2003) 79
2. Crépy K.V.L., and Imamoto T. Top. Curr. Chem. 229 (2003) 1
3. Tang W., and Zhang X. Chem. Rev. 103 (2003) 3029
4. Zhang W., Chi Y., and Zhang X. Acc. Chem. Res. 40 (2007) 1278
5. Imamoto T., Watanabe J., Wada Y., Masuda H., Yamada H., Tsuruta H., Matsukawa S., and Yamaguchi K. J. Am. Chem. Soc. 120 (1998) 1635
6. Gridnev I.D., Yamanoi Y., Higashi N., Tsuruta H., Yasutake M., and Imamoto T. Adv. Synth. Catal. 343 (2001) 118
7. Yamanoi Y., and Imamoto T. J. Org. Chem. 64 (1999) 2988
8. Imamoto T., Sugita K., and Yoshida K. J. Am. Chem. Soc. 127 (2005) 11934
9. Tang W., and Zhang Z. Angew. Chem., Int. Ed. 41 (2002) 1612
10. Muci A.R., Campos K.R., and Evans D.A. J. Am. Chem. Soc. 117 (1995) 9075
11. Wolfe B., and Livinghouse T. J. Am. Chem. Soc. 120 (1998) 5116
12. Dearden M.J., McGrath M.J., and O'Brien P. J. Org. Chem. 69 (2004) 5789
13. Headley C.E., and Marsden S.P. J. Org. Chem. 72 (2007) 7185
14. 3).
15. + 169.1288, found 169.1295.
16. We have a number of examples in our group where the conversion of phosphine boranes into phosphine sulfides using DABCO and sulfur in toluene at 80 °C proceeds with no loss of er.