Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate

Buhr S, Griesbeck AG, Lex J, Mattay J, Schroer J (1996)
Tetrahedron Letters 37(8): 1195-1196.

Journal Article | Published | English

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Abstract
Photocycloaddition of 2,2-diisopropyl:1,3-dioxol (1) with methyl trimethylpyruvate (2c) leads to the bicyclic oxetane 3c in high (> 98%) diastereoisomeric excess. X-ray analysis of 39 revealed the endo-tert.-butyl configuration. Semiempirical calculations (AM1) indicate that kinetic product control exists which can be rationalized with spin-orbit coupling elements.
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Buhr S, Griesbeck AG, Lex J, Mattay J, Schroer J. Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate. Tetrahedron Letters. 1996;37(8):1195-1196.
Buhr, S., Griesbeck, A. G., Lex, J., Mattay, J., & Schroer, J. (1996). Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate. Tetrahedron Letters, 37(8), 1195-1196.
Buhr, S., Griesbeck, A. G., Lex, J., Mattay, J., and Schroer, J. (1996). Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate. Tetrahedron Letters 37, 1195-1196.
Buhr, S., et al., 1996. Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate. Tetrahedron Letters, 37(8), p 1195-1196.
S. Buhr, et al., “Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate”, Tetrahedron Letters, vol. 37, 1996, pp. 1195-1196.
Buhr, S., Griesbeck, A.G., Lex, J., Mattay, J., Schroer, J.: Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate. Tetrahedron Letters. 37, 1195-1196 (1996).
Buhr, S, Griesbeck, AG, Lex, J, Mattay, Jochen, and Schroer, J. “Electronic control of stereoselectivity in photocycloaddition reactions .7. Stereoselectivity in the Paterno-Buchi reaction of 2,2-diisopropyl-1,3-dioxol with methyl trimethylpyruvate”. Tetrahedron Letters 37.8 (1996): 1195-1196.
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