Regioselective hydrostannation of allenes catalyzed by Pd(OH)2/C

Tetrahedron Letters

Volumn 38, Issue 36, 1997, Pages 6343-6346

  Lautens, Mark ^a   Ostrovsky, Dennis ^a   Tao, Beata ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOTIN COMPOUND;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030798695     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01459-7     Document Type: Article

References (23)

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10. Palladium (O) also catalyzes the addition of carbon "pronucleophiles" to allenes to give products equivalent to allylic substitution, see: Trost, B.M.; Gerusz, V.J. J. Am. Chem. Soc. 1995, 117, 5156.
11. e) Palladium catalyzed addition to the central carbon of an allene followed by cyclization is known, see: Larock, R.C.; Berrios-Pena, N.G.; Fried, C.A. J. Org. Chem. 1991, 56, 2615. In this study the mechanism is proposed to occur via carbopalladation to form a π-allyl intermediate which is analogous to intermediates 23 and 25 in Scheme 4
12. f) Following the submission of our manuscript, Yamamoto reported palladium and Lewis acid catalysts are useful for the preparation of allyl and vinylstannanes, see: Gevorgyan, V.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2963.
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15. Thomas has reported that enantiopure (alkoxyallyl)stannanes related to those obtained in our study react with aldehydes in the presence of SnCl4 to give efficient 1,5-asymmetric induction, see: Thomas, E.J. in Stereocontrolled Organic Synthesis, ed. Trost, B.M., Blackwell, 1994, pp. 235 and J. Chem. Soc., Chem. Commun. 1997, 411.
16. Thomas has reported that enantiopure (alkoxyallyl)stannanes related to those obtained in our study react with aldehydes in the presence of SnCl4 to give efficient 1,5-asymmetric induction, see: Thomas, E.J. in Stereocontrolled Organic Synthesis, ed. Trost, B.M., Blackwell, 1994, pp. 235 and J. Chem. Soc., Chem. Commun. 1997, 411.
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