Stereocontrolled Preparation of 2,6-Disubstituted 4-Methylenetetrahydropyrans by Lewis Acid Promoted Allylsilane-Acetal Cyclization

Bulletin of the Korean Chemical Society

Volumn 19, Issue 8, 1998, Pages 862-868

  Sung, Tae Myung ^a   Kwak, Woo Young ^a   Kang, Kyung Tae ^a  

^a Pusan National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010132441     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

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11. (b) 2,6-Dialkyl-3-hydroxy-4-methylenetetrahydropyrans were also prepared from the ISMS reaction of 2-(trimethylsiloxymethyl)allyltrimethylsilane with aliphatic aldehydes, however, 2,6-diaryl derivatives could not be obtained under the same reaction conditions: Marko, I. E.; Bayston, D. J. Tetrahedron Lett. 1993, 34, 6595.
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14. 2-Stannyl-3-silylpropene: (a) Kang, K. -T.; Kim, S. S.; Lee, J. C. Tetrahedron Lett. 1991, 32, 4341. (b) Kang, K. -T.; Kim, S. S.; Lee, J. C.; U, J. S. Tetrahedron Lett. 1992, 33, 3495. (c) 3-Stannyl-2-(silylmethyl)propene: Kang, K. -T.; U, J. S.; Park, D. K.; Kim, J. K.; Kim, W. J. Bull. Korean Chem. Soc. 1995, 16, 464.
15. Bismetallic reagent 1 is considerably more reactive than simple allylstannanes due to the extra activation (β-effect) provided by the allylic silyl substituent. Kang, K.-T.; Sung, T. M.; Kim, J. K.; Kwon, Y. M. Synth. Commum. 1997, 27, 1173.
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