Preparation of (R)-Fluoropyruvaldehyde N,S-Ketals by Highly Stereospecific Tandem Pummerer Rearrangement/1,2-p-Tolylthio Group Migration of (R)-α-(Fluoroalkyl)-β-sulfinylenamines

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 8031-8040

  Volonterio, Alessandro ^a   Zanda, Matteo ^a   Bravo, Pierfrancesco ^b   Fronza, Giovanni ^b   Cavicchio, Giancarlo ^c   Crucianelli, Marcello ^c  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

^c UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001621168     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970863j     Document Type: Article

References (76)

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32. For a very recent work on the diastereoselectivity of the indium-promoted allylation of both N-monoprotected α-amino and α-sulfenyl aldehydes: (i) Paquette, L. A.; Mitzel, T. M.; Isaac, M. B.; Crasto, C. F.; Schomer, W. W. J. Org. Chem. 1997, 62, 4293.
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40. Tsuchihashi and Ogura reported a rearrangement of racemic N-unprotected β-methylthio β-sulfinylenamines K (Scheme 6), promoted by acetic anhydride in the presence of pyridine, producing the thiolesters L. To our knowledge no details have appeared on the mechanism of that process, which presents several analogies with the title reaction, (a) Ogura, K.; Tsuchihashi, G. J. Am. Chem. Soc. 1974, 96, 1960.
41. See also: (b) Ogura, K.; Ito, Y.; Tsuchihashi, G. Bull. Chem. Soc. Jpn. 1979, 52, 2013.
42. The absolute stereochemistries of the intermediate imines (R)-3 are confidently assigned on the basis of the mechanistic rationale discussed onward.
43. An alternative racemization path involves the equilibrium between the F-PAKs 2 and the α-hydroxy imine form 11 (Scheme 12).
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59. DCC has been used as a scavenger of acyloxy anions, sometimes producing a remarkable improvement of stereoselection, but also a dramatic lowering of yields: (a) Stridsberg, B.; Allenmark, S. Acta Chem. Scand. 1976, B30, 219. (b) Numata, T.; Itoh, O.; Oae, S. Tetrahedron Lett. 1979, 20, 1869. (c) Numata, T.; Itoh, O.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 257. (d) Itoh, O.; Numata, T.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 266. (e) Oae, S., Itoh, O.; Numata, T.; Yoshimura, T. Bull. Chem. Soc. Jpn. 1983, 56, 270.
60. DCC has been used as a scavenger of acyloxy anions, sometimes producing a remarkable improvement of stereoselection, but also a dramatic lowering of yields: (a) Stridsberg, B.; Allenmark, S. Acta Chem. Scand. 1976, B30, 219. (b) Numata, T.; Itoh, O.; Oae, S. Tetrahedron Lett. 1979, 20, 1869. (c) Numata, T.; Itoh, O.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 257. (d) Itoh, O.; Numata, T.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 266. (e) Oae, S., Itoh, O.; Numata, T.; Yoshimura, T. Bull. Chem. Soc. Jpn. 1983, 56, 270.
61. DCC has been used as a scavenger of acyloxy anions, sometimes producing a remarkable improvement of stereoselection, but also a dramatic lowering of yields: (a) Stridsberg, B.; Allenmark, S. Acta Chem. Scand. 1976, B30, 219. (b) Numata, T.; Itoh, O.; Oae, S. Tetrahedron Lett. 1979, 20, 1869. (c) Numata, T.; Itoh, O.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 257. (d) Itoh, O.; Numata, T.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 266. (e) Oae, S., Itoh, O.; Numata, T.; Yoshimura, T. Bull. Chem. Soc. Jpn. 1983, 56, 270.
62. DCC has been used as a scavenger of acyloxy anions, sometimes producing a remarkable improvement of stereoselection, but also a dramatic lowering of yields: (a) Stridsberg, B.; Allenmark, S. Acta Chem. Scand. 1976, B30, 219. (b) Numata, T.; Itoh, O.; Oae, S. Tetrahedron Lett. 1979, 20, 1869. (c) Numata, T.; Itoh, O.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 257. (d) Itoh, O.; Numata, T.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 266. (e) Oae, S., Itoh, O.; Numata, T.; Yoshimura, T. Bull. Chem. Soc. Jpn. 1983, 56, 270.
63. DCC has been used as a scavenger of acyloxy anions, sometimes producing a remarkable improvement of stereoselection, but also a dramatic lowering of yields: (a) Stridsberg, B.; Allenmark, S. Acta Chem. Scand. 1976, B30, 219. (b) Numata, T.; Itoh, O.; Oae, S. Tetrahedron Lett. 1979, 20, 1869. (c) Numata, T.; Itoh, O.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 257. (d) Itoh, O.; Numata, T.; Yoshimura, T.; Oae, S. Bull. Chem. Soc. Jpn. 1983, 56, 266. (e) Oae, S., Itoh, O.; Numata, T.; Yoshimura, T. Bull. Chem. Soc. Jpn. 1983, 56, 270.
64. The deprotonation step of the PR has been elegantly studied by Kita and Shibata, who used O-silylated ketene acetals for achieving excellent stereocontrol: Kita, Y.; Shibata, N. Synlett 1996, 289 and references therein.
65. For a discussion on this eventuality see: Kita, Y.; Shibata, N.; Fukui, S.; Fujita, S. Tetrahedron Lett. 1994, 35, 9733 and references therein.
66. For some examples of neighboring group participation by amino junctions under Pummerer conditions see: (a) Sharma, A. K.; Ku, T.; Dawson, A. D.; Swern, D. J. Org. Chem. 1975, 40, 2758. (b) Yamamoto, K.; Yamazaki, S.; Murata, I.; Fukuzawa, Y. J. Org. Chem. 1987, 52, 5239 (c) Uchida, Y.; Oae, S. Gazz. Chim. Ital. 1987, 117, 649. (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc., Perkin Trans. 1 1995, 2405. See also ref 19i.
67. For some examples of neighboring group participation by amino junctions under Pummerer conditions see: (a) Sharma, A. K.; Ku, T.; Dawson, A. D.; Swern, D. J. Org. Chem. 1975, 40, 2758. (b) Yamamoto, K.; Yamazaki, S.; Murata, I.; Fukuzawa, Y. J. Org. Chem. 1987, 52, 5239 (c) Uchida, Y.; Oae, S. Gazz. Chim. Ital. 1987, 117, 649. (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc., Perkin Trans. 1 1995, 2405. See also ref 19i.
68. For some examples of neighboring group participation by amino junctions under Pummerer conditions see: (a) Sharma, A. K.; Ku, T.; Dawson, A. D.; Swern, D. J. Org. Chem. 1975, 40, 2758. (b) Yamamoto, K.; Yamazaki, S.; Murata, I.; Fukuzawa, Y. J. Org. Chem. 1987, 52, 5239 (c) Uchida, Y.; Oae, S. Gazz. Chim. Ital. 1987, 117, 649. (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc., Perkin Trans. 1 1995, 2405. See also ref 19i.
69. For some examples of neighboring group participation by amino junctions under Pummerer conditions see: (a) Sharma, A. K.; Ku, T.; Dawson, A. D.; Swern, D. J. Org. Chem. 1975, 40, 2758. (b) Yamamoto, K.; Yamazaki, S.; Murata, I.; Fukuzawa, Y. J. Org. Chem. 1987, 52, 5239 (c) Uchida, Y.; Oae, S. Gazz. Chim. Ital. 1987, 117, 649. (d) Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc., Perkin Trans. 1 1995, 2405. See also ref 19i.
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71. We thank Prof. Józef Drabowicz (Polish Academy of Sciences, Lodz, Poland) who suggested to us that the low enantioselectivity featured by the diF-PAK (R)-E-1d could have been due to racemization of the sulfinyl stereocenter by action of TFAA.
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