Nitrite anion cyclization with epoxysilanes followed by Brook rearrangement/ring opening of cyclopropane nitriles/alkylation

Organic Letters

Volumn 6, Issue 17, 2004, Pages 2973-2975

  Okugawa, Seigo ^a   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENT; ANION; BASE; CYCLOPROPANE DERIVATIVE; NITRILE; SILANE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; ISOMERIZATION; RING OPENING; STEREOCHEMISTRY;

EID: 4444346488     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048817a     Document Type: Article

References (23)

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6. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
7. For reviews on the Brook rearrangement, see: (a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, John Wiley & Sons: New York, 2000. (b) Brook, A. G.; Bassindale, A. R. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; pp 149-221. (c) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
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9. Also see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
10. Also see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
11. Also see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
12. Also see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
13. Also see: (e) Ricci, A.; Degl'Innocenti, A. Synthesis 1989, 647-660. (f) Bulman Page, P. C.; Klair, S. S.; Rosenthal, S. Chem. Soc. Rev. 1990, 19, 147-195. (g) Qi, H.; Curran, D. P. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Moody, C. J., Eds.; Pergamon: Oxford, 1995; pp 409-431. (h) Cirillo, P. F.; Panek, J. S. Org. Prep. Proc. Int. 1992, 24, 553-582. (i) Patrocinio, A. F.; Moran, P. J. S. J. Braz. Chem. Soc. 2001, 12, 7-31.
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22. Dialkylation was a major side reaction in the alkylation step of lithiomalononitrile.
23. Elimination reactions of α-oxidosilanes with a β-leaving group are known to proceed in an anti manner. Hudrlik, P. F.; Hudrlik, A. M.; Kulkarni, A. K. J. Am. Chem. Soc. 1985, 107, 4260-4264.