Highly stereoselective Saucy-Marbet rearrangement using chiral ynamides. Synthesis of highly substituted chiral homoallenyl alcohols

Organic Letters

Volumn 5, Issue 15, 2003, Pages 2663-2666

  Frederick, Michael O ^a   Hsung, Richard P ^a   Lambeth, Robert H ^a   Mulder, Jason A ^a   Tracey, Michael R ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALLENE DERIVATIVE; AMIDE; NITROBENZENE DERIVATIVE; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0141631540     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol030061c     Document Type: Article

References (58)

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48. D.
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51. 2 groups.
52. 2 = c-hex.
53. For some examples, see: (a) Trost, B. M.; Pinkerton, A. B.; Seidel, M. J. Am. Chem. Soc. 2001, 123, 12466. (b) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441. (c) Oh, C. H.; Rhim, C. Y. ; Song, C. H.; Ryu, J. H. Chem. Lett. 2002, 1140. (d) Yoneda, E.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Tetrahedron Lett. 2001, 42, 5459. (e) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104. (f) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
54. For some examples, see: (a) Trost, B. M.; Pinkerton, A. B.; Seidel, M. J. Am. Chem. Soc. 2001, 123, 12466. (b) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441. (c) Oh, C. H.; Rhim, C. Y. ; Song, C. H.; Ryu, J. H. Chem. Lett. 2002, 1140. (d) Yoneda, E.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Tetrahedron Lett. 2001, 42, 5459. (e) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104. (f) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
55. For some examples, see: (a) Trost, B. M.; Pinkerton, A. B.; Seidel, M. J. Am. Chem. Soc. 2001, 123, 12466. (b) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441. (c) Oh, C. H.; Rhim, C. Y. ; Song, C. H.; Ryu, J. H. Chem. Lett. 2002, 1140. (d) Yoneda, E.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Tetrahedron Lett. 2001, 42, 5459. (e) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104. (f) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
56. For some examples, see: (a) Trost, B. M.; Pinkerton, A. B.; Seidel, M. J. Am. Chem. Soc. 2001, 123, 12466. (b) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441. (c) Oh, C. H.; Rhim, C. Y. ; Song, C. H.; Ryu, J. H. Chem. Lett. 2002, 1140. (d) Yoneda, E.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Tetrahedron Lett. 2001, 42, 5459. (e) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104. (f) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
57. For some examples, see: (a) Trost, B. M.; Pinkerton, A. B.; Seidel, M. J. Am. Chem. Soc. 2001, 123, 12466. (b) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441. (c) Oh, C. H.; Rhim, C. Y. ; Song, C. H.; Ryu, J. H. Chem. Lett. 2002, 1140. (d) Yoneda, E.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Tetrahedron Lett. 2001, 42, 5459. (e) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104. (f) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
58. For some examples, see: (a) Trost, B. M.; Pinkerton, A. B.; Seidel, M. J. Am. Chem. Soc. 2001, 123, 12466. (b) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Org. Lett. 2000, 2, 441. (c) Oh, C. H.; Rhim, C. Y. ; Song, C. H.; Ryu, J. H. Chem. Lett. 2002, 1140. (d) Yoneda, E.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Tetrahedron Lett. 2001, 42, 5459. (e) Ma, S.; Gao, W. J. Org. Chem. 2002, 67, 6104. (f) Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.