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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 22
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Original Articles

Tin Effects in the Hydroboration of Hindered Olefins

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Pages 3453-3458 | Received 08 Oct 1990, Published online: 24 Oct 2006

References

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  • The ratio is based on limits of nmr analysis, no attempt was made to factor into the ratio the two equivalent sites for addition to 2,3-dimethyl-2-butene versus the one for the allyltin substrate
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  • Assuming the trialkylstannane group is equatorial, the isomeric boron adduct would form the trans diaxial diol on oxidation and a mixture of acyclic carbonates on reaction with 1,1′-carbonyldiimidazole
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  • Fleming , I. and Lawrence , N. J. 1988 . Tetrahedron Let. , 29 : 2077 – 80 . The relative stereochemistry shown has been tentatively assigned based on anti addition of boron to the allylic tin or silicon group through the presumed most stable conformation analogous to the Fleming model, see:
  • Marshall , J. A. and Flynn , K. E. 1984 . J. Am. Chem. Soc. , 106 : 723 – 30 .
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