p-siletanylbenzylidene acetal: Oxidizable Protecting group for diols

Journal of Organic Chemistry

Volumn 71, Issue 1, 2006, Pages 420-422

  House, Sarah E ^a   Poon, Kevin W C ^a   Lam, Hubert ^a   Dudley, Gregory B ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; HYDROGEN PEROXIDE; NITROGEN COMPOUNDS; OXIDATION; REDUCTION; RING OPENING POLYMERIZATION; STEREOCHEMISTRY;

BENZYLIDENE ACETALS; HYDROGEN PEROXIDE OXIDATION; REGIOSELECTIVE REDUCTION;

ETHERS;

BENZYLIDENEACETONE; HYDROGEN PEROXIDE;

ARTICLE; DEPROTECTION REACTION; OXIDATION; REDUCTION; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 31144454147     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052015r     Document Type: Article

References (18)

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4. (b) Kocienski, P. J. Protecting Groups, 3rd ed.; Thieme: Stuttgart, Germany, 2003.
5. Preparative Carbohydrate Chemistry, Hanessian, S., Ed.; Marcel Dekker: New York, 1997.
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12. Siletanes withstand DIBAL-H but decompose in the presence of lithium aluminum hydride.
13. Prepared in two steps and 93% overall yield. See the Supporting Information.
14. Mikami, T.; Asano, H.; Mitsunobu, O. Chem. Lett. 1987, 2033-2036.
15. The reaction vessel was placed in the freezer overnight. See the Supporting Information.
16. 2O, 20 °C), NaOMe (MeOH, 60 °C), etc.; see ref 6a.
17. For example, iron trichloride in ether is effective. See the Supporting Information.
18. The conversion from 1 to 12 is essentially quantitative, but our starting material (1) was contaminated with a small amount of 12 from incidental hydrolysis that had occurred upon prolonged storage.