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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 15
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Original Articles

The Stereochemistry of the Reaction of α-Silyl Lithium Reagents with Cyclic Tert-butyldimethylsilyl Acyloins

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Pages 2773-2778 | Received 01 May 1989, Published online: 24 Oct 2006

References

  • Taken in part from the doctoral dissertation of P. G. University of Puerto Rico . Río Piedras campus
  • University of Puerto Rico .
  • Hüls America, Inc./Petrarch Systems
  • 1981–1986 . NIGMS-MARC Faculty Fellow ,
  • Koreeda , M. , Patel , P. D. and Brown , L. 1985 . J. Org. Chem. , 50 : 5912
  • Garner , P. and Ramakanth , S. 1987 . Ibid. , 52 : 2629
  • Larson , G. L. , Prieto , J. A. and Hernández , A. 1981 . Tetrahedron Lett. , 22 : 1575
  • Brook , A. G. , Duff , J. M. and Anderson , D. G. 1970 . J. Amer. Chem. Soc. , 92 : 7567
  • Carey , F. A. and Court , A. S. 1972 . J. Org. Chem. , 37 : 939
  • Zimmerman , H. E. and Klun , R. T. 1978 . Tetrahedron , 34 : 1775
  • 4a (n=0); 4b (n=1); 4c (n=2); 5a (n=0, Y=Ph); 5b (n-0, Y=SPh); 5c (n=0, Y=CN); 5d (n=1, Y=Ph); 5e (n=1, Y=SPh); 5f (n=1, Y=CN); 5g (n=2, Y=Ph), 5h (n=2, Y=SPh); 5i (n=2, Y=CN). Chemical shifts, δ, for the vinyl protons: (Z) 5a 6.40, (E) 5a 6.48; (Z) 5b 6.21, (E) 5b 6.13; (Z) 5c 5.34, (E) 5c 5.29; (Z) 5d 6.65, (E) 5d 6.49; (Z) 5e 5.84, (E) 5e 6.28; (Z) 5f 5.01, (E) 5f 5.41; (Z) 5g 6.71, (E) 5g 6.50; (Z) 5h 5.88, (E) 5h 5.57; (Z) 5i 5.08, (E) 5i 5.51

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