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On the unexpected stereochemical outcome of the magnesium in methanol : conjugate reduction of an exocyclic alpha,beta-unsaturated ester

Stefan Gabriels, Dirk Van Haver (UGent) , Maurits Vandewalle, Pierre De Clercq (UGent) and Davide Viterbo
(1999) EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 1999(8). p.1803-1809
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Organization
Abstract
The conjugate reduction of the exocyclic alpha,beta-unsaturated ester 9 with magnesium in methanol gives a mixture of diastereoisomers containing predominantly the less stable 10a. Eventual structural identification rests on the X-ray diffraction analysis of tosylate 18.
Keywords
magnesium-methanol reduction, reductions, alpha,beta-unsaturated esters, stereoselectivity, (R)-(-)-carvone, analogs of 1 alpha,25-(OH)(2)-vitamin D-3, steroids, VITAMIN-D ANALOGS, D-RING ANALOGS, D ENDOCRINE SYSTEM, CD-RING, D CALCIFEROL, CONFORMATION, MOLECULES, KETONES, D-3

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MLA
Gabriels, Stefan, et al. “On the Unexpected Stereochemical Outcome of the Magnesium in Methanol : Conjugate Reduction of an Exocyclic Alpha,Beta-Unsaturated Ester.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 1999, no. 8, 1999, pp. 1803–09, doi:10.1002/(SICI)1099-0690(199908)1999:8<1803::AID-EJOC1803>3.0.CO;2-L.
APA
Gabriels, S., Van Haver, D., Vandewalle, M., De Clercq, P., & Viterbo, D. (1999). On the unexpected stereochemical outcome of the magnesium in methanol : conjugate reduction of an exocyclic alpha,beta-unsaturated ester. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999(8), 1803–1809. https://doi.org/10.1002/(SICI)1099-0690(199908)1999:8<1803::AID-EJOC1803>3.0.CO;2-L
Chicago author-date
Gabriels, Stefan, Dirk Van Haver, Maurits Vandewalle, Pierre De Clercq, and Davide Viterbo. 1999. “On the Unexpected Stereochemical Outcome of the Magnesium in Methanol : Conjugate Reduction of an Exocyclic Alpha,Beta-Unsaturated Ester.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 1999 (8): 1803–9. https://doi.org/10.1002/(SICI)1099-0690(199908)1999:8<1803::AID-EJOC1803>3.0.CO;2-L.
Chicago author-date (all authors)
Gabriels, Stefan, Dirk Van Haver, Maurits Vandewalle, Pierre De Clercq, and Davide Viterbo. 1999. “On the Unexpected Stereochemical Outcome of the Magnesium in Methanol : Conjugate Reduction of an Exocyclic Alpha,Beta-Unsaturated Ester.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 1999 (8): 1803–1809. doi:10.1002/(SICI)1099-0690(199908)1999:8<1803::AID-EJOC1803>3.0.CO;2-L.
Vancouver
1.
Gabriels S, Van Haver D, Vandewalle M, De Clercq P, Viterbo D. On the unexpected stereochemical outcome of the magnesium in methanol : conjugate reduction of an exocyclic alpha,beta-unsaturated ester. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 1999;1999(8):1803–9.
IEEE
[1]
S. Gabriels, D. Van Haver, M. Vandewalle, P. De Clercq, and D. Viterbo, “On the unexpected stereochemical outcome of the magnesium in methanol : conjugate reduction of an exocyclic alpha,beta-unsaturated ester,” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 1999, no. 8, pp. 1803–1809, 1999.
@article{112119,
  abstract     = {{The conjugate reduction of the exocyclic alpha,beta-unsaturated ester 9 with magnesium in methanol gives a mixture of diastereoisomers containing predominantly the less stable 10a. Eventual structural identification rests on the X-ray diffraction analysis of tosylate 18.}},
  author       = {{Gabriels, Stefan and Van Haver, Dirk and Vandewalle, Maurits and De Clercq, Pierre and Viterbo, Davide}},
  issn         = {{1434-193X}},
  journal      = {{EUROPEAN JOURNAL OF ORGANIC CHEMISTRY}},
  keywords     = {{magnesium-methanol reduction,reductions,alpha,beta-unsaturated esters,stereoselectivity,(R)-(-)-carvone,analogs of 1 alpha,25-(OH)(2)-vitamin D-3,steroids,VITAMIN-D ANALOGS,D-RING ANALOGS,D ENDOCRINE SYSTEM,CD-RING,D CALCIFEROL,CONFORMATION,MOLECULES,KETONES,D-3}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{1803--1809}},
  title        = {{On the unexpected stereochemical outcome of the magnesium in methanol : conjugate reduction of an exocyclic alpha,beta-unsaturated ester}},
  url          = {{http://doi.org/10.1002/(SICI)1099-0690(199908)1999:8<1803::AID-EJOC1803>3.0.CO;2-L}},
  volume       = {{1999}},
  year         = {{1999}},
}
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