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Bertozzi F, Pineschi M, Macchia F, et al. Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol. Org Lett. 2002;4(16):2703-5doi: 10.1021/ol026220u.
Bertozzi, F., Pineschi, M., Macchia, F., Arnold, L. A., Minnaard, A. J., & Feringa, B. L. (2002). Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol. Organic letters, 4(16), 2703-5. https://doi.org/10.1021/ol026220u
Bertozzi, Fabio, et al. "Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol." Organic letters vol. 4,16 (2002): 2703-5. doi: https://doi.org/10.1021/ol026220u
Bertozzi F, Pineschi M, Macchia F, Arnold LA, Minnaard AJ, Feringa BL. Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol. Org Lett. 2002 Aug 08;4(16):2703-5. doi: 10.1021/ol026220u. PMID: 12153214.
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Org Lett. 2002 Aug 08;4(16):2703-5. doi: 10.1021/ol026220u.

Copper phosphoramidite catalyzed enantioselective ring-opening of oxabicyclic alkenes: remarkable reversal of stereocontrol.

Organic letters

Fabio Bertozzi, Mauro Pineschi, Franco Macchia, Leggy A Arnold, Adriaan J Minnaard, Ben L Feringa

Affiliations

  1. Department of Organic and Molecular Inorganic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, The Netherlands.

PMID: 12153214 DOI: 10.1021/ol026220u

Abstract

[reaction: see text] An unprecedented copper phosphoramidite catalyzed enantioselective alkylative ring-opening reaction of oxabenzonorbornadiene derivatives with dialkylzinc reagents is reported. The reaction shows high levels of anti-stereoselectivity (up to anti/syn >99:1), complementary to the Pd(0)-catalyzed syn-selective ring-opening protocol, allowing a new entry to anti-dihydronaphthols with high enantioselectivity (up to 99% ee).

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