Asymmetric α-alkylation of N′-tert-butanesulfinyl amidines. Application to the total synthesis of (6 R,7 S)-7-amino-7,8-dihydro-α- bisabolene

Journal of the American Chemical Society

Volumn 126, Issue 48, 2004, Pages 15652-15653

  Kochi, Takuya ^a   Ellman, Jonathan A ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 AMINO 7,8 DIHYDRO ALPHA BISABOLENE; AMIDINE; BISABOLOL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMISTRY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 10044231521     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044753n     Document Type: Article

References (24)

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6. For additions to tert-butanesulfinyl imines, see: (a) Ellman, J. A.; Owens. T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995. (b) Kochi, T.; Mukade, T.; Ellman, J. A. J. Synth. Org. Chem., Jpn. 2004, 62, 128-139. (c) Higashibayashi, S.; Kohno, M.; Goto, T.; Suzuki, K.; Mori, T.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2004, 45, 3707. (d) DeSolms, S. J.; Ciccarone, T. M.; MacTough, S. C. et al. J. Med. Chem. 2003, 46, 2973. (e) Jung, P. M.; Beaudegnies, E.; DeMesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297. (f) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641-6643. (g) Pflum, D. A.; Krishnamurthy, D.; Han, Z.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923-926.
7. For additions to tert-butanesulfinyl imines, see: (a) Ellman, J. A.; Owens. T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995. (b) Kochi, T.; Mukade, T.; Ellman, J. A. J. Synth. Org. Chem., Jpn. 2004, 62, 128-139. (c) Higashibayashi, S.; Kohno, M.; Goto, T.; Suzuki, K.; Mori, T.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2004, 45, 3707. (d) DeSolms, S. J.; Ciccarone, T. M.; MacTough, S. C. et al. J. Med. Chem. 2003, 46, 2973. (e) Jung, P. M.; Beaudegnies, E.; DeMesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297. (f) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641-6643. (g) Pflum, D. A.; Krishnamurthy, D.; Han, Z.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923-926.
8. For additions to tert-butanesulfinyl imines, see: (a) Ellman, J. A.; Owens. T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995. (b) Kochi, T.; Mukade, T.; Ellman, J. A. J. Synth. Org. Chem., Jpn. 2004, 62, 128-139. (c) Higashibayashi, S.; Kohno, M.; Goto, T.; Suzuki, K.; Mori, T.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2004, 45, 3707. (d) DeSolms, S. J.; Ciccarone, T. M.; MacTough, S. C. et al. J. Med. Chem. 2003, 46, 2973. (e) Jung, P. M.; Beaudegnies, E.; DeMesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297. (f) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641-6643. (g) Pflum, D. A.; Krishnamurthy, D.; Han, Z.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923-926.
9. For additions to tert-butanesulfinyl imines, see: (a) Ellman, J. A.; Owens. T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995. (b) Kochi, T.; Mukade, T.; Ellman, J. A. J. Synth. Org. Chem., Jpn. 2004, 62, 128-139. (c) Higashibayashi, S.; Kohno, M.; Goto, T.; Suzuki, K.; Mori, T.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2004, 45, 3707. (d) DeSolms, S. J.; Ciccarone, T. M.; MacTough, S. C. et al. J. Med. Chem. 2003, 46, 2973. (e) Jung, P. M.; Beaudegnies, E.; DeMesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297. (f) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641-6643. (g) Pflum, D. A.; Krishnamurthy, D.; Han, Z.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923-926.
10. For additions to tert-butanesulfinyl imines, see: (a) Ellman, J. A.; Owens. T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995. (b) Kochi, T.; Mukade, T.; Ellman, J. A. J. Synth. Org. Chem., Jpn. 2004, 62, 128-139. (c) Higashibayashi, S.; Kohno, M.; Goto, T.; Suzuki, K.; Mori, T.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2004, 45, 3707. (d) DeSolms, S. J.; Ciccarone, T. M.; MacTough, S. C. et al. J. Med. Chem. 2003, 46, 2973. (e) Jung, P. M.; Beaudegnies, E.; DeMesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297. (f) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641-6643. (g) Pflum, D. A.; Krishnamurthy, D.; Han, Z.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923-926.
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12. For additions to tert-butanesulfinyl imines, see: (a) Ellman, J. A.; Owens. T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984-995. (b) Kochi, T.; Mukade, T.; Ellman, J. A. J. Synth. Org. Chem., Jpn. 2004, 62, 128-139. (c) Higashibayashi, S.; Kohno, M.; Goto, T.; Suzuki, K.; Mori, T.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2004, 45, 3707. (d) DeSolms, S. J.; Ciccarone, T. M.; MacTough, S. C. et al. J. Med. Chem. 2003, 46, 2973. (e) Jung, P. M.; Beaudegnies, E.; DeMesmaeker, A.; Wendeborn, S. Tetrahedron Lett. 2003, 44, 293-297. (f) Kuduk, S. D.; DiPardo, R. M.; Chang, R. K.; Ng, C.; Bock, M. G. Tetrahedron Lett. 2004, 45, 6641-6643. (g) Pflum, D. A.; Krishnamurthy, D.; Han, Z.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 2002, 43, 923-926.
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