Reactions of homoallylstannanes with carbon electrophiles: Stereoselective cyclopropylmethylation based on the γ-effect of tin

Chemical Communications

Volumn , Issue 6, 1999, Pages 505-506

  Sugawara, Masanobu ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ACID; ALDEHYDE; ALLYL COMPOUND; CARBON; CHLORIDE; CYCLOPROPANE DERIVATIVE; TIN;

ARTICLE; CHEMICAL REACTION; ELECTRIC ACTIVITY; METHYLATION; STEREOCHEMISTRY;

EID: 0033590755     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a900228f     Document Type: Article

References (21)

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11. Cyclopropylmethylations with hetero-electrophiles by homoallylstannanes have been reported: D. J. Peterson and M. D. Robbins, Tetrahedron Lett., 1972, 2135; D. J. Paterson, M. D. Robbins and J. R. Hansen, J. Organomet. Chem., 1974, 73, 237; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; Y. Ueno, M. Ohta and M. Okawara, Tetrahedron Lett., 1982, 23, 2577; J. W. Herndon and J. J. Harp, Tetrahedron Lett., 1992, 33, 6243.
12. Cyclopropylmethylations with hetero-electrophiles by homoallylstannanes have been reported: D. J. Peterson and M. D. Robbins, Tetrahedron Lett., 1972, 2135; D. J. Paterson, M. D. Robbins and J. R. Hansen, J. Organomet. Chem., 1974, 73, 237; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; Y. Ueno, M. Ohta and M. Okawara, Tetrahedron Lett., 1982, 23, 2577; J. W. Herndon and J. J. Harp, Tetrahedron Lett., 1992, 33, 6243.
13. Cyclopropylmethylations with hetero-electrophiles by homoallylstannanes have been reported: D. J. Peterson and M. D. Robbins, Tetrahedron Lett., 1972, 2135; D. J. Paterson, M. D. Robbins and J. R. Hansen, J. Organomet. Chem., 1974, 73, 237; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; Y. Ueno, M. Ohta and M. Okawara, Tetrahedron Lett., 1982, 23, 2577; J. W. Herndon and J. J. Harp, Tetrahedron Lett., 1992, 33, 6243.
14. Cyclopropylmethylations with hetero-electrophiles by homoallylstannanes have been reported: D. J. Peterson and M. D. Robbins, Tetrahedron Lett., 1972, 2135; D. J. Paterson, M. D. Robbins and J. R. Hansen, J. Organomet. Chem., 1974, 73, 237; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; Y. Ueno, M. Ohta and M. Okawara, Tetrahedron Lett., 1982, 23, 2577; J. W. Herndon and J. J. Harp, Tetrahedron Lett., 1992, 33, 6243.
15. Cyclopropylmethylations with hetero-electrophiles by homoallylstannanes have been reported: D. J. Peterson and M. D. Robbins, Tetrahedron Lett., 1972, 2135; D. J. Paterson, M. D. Robbins and J. R. Hansen, J. Organomet. Chem., 1974, 73, 237; K. C. Nicolaou, D. A. Claremon, W. E. Barnette and S. P. Seitz, J. Am. Chem. Soc., 1979, 101, 3704; Y. Ueno, M. Ohta and M. Okawara, Tetrahedron Lett., 1982, 23, 2577; J. W. Herndon and J. J. Harp, Tetrahedron Lett., 1992, 33, 6243.
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19. The erythro stereochemistry was determined by comparison with an authentic sample, which was prepared by the cyclopropanation of the corresponding homoallylalcohol.
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