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2005
Nitrile formation
O 0273
Synthesis of Highly Functionalized Chiral Nitriles by Radical Fragmentation of
Azides. Convenient Transformation of Aldononitriles into 1,4- and
16- 053 β-Hydroxy
1,5-Iminoalditols. — Treatment of various β-hydroxy azides of carbohydrates with
PhI(OAc)2/I2 results in formation of aldononitriles which are useful precursors of
1,4- and 1,5-iminoalditols. Other carbocyclic β-hydroxy azides such as terpene and steroid derivatives also undergo radical fragmentation yielding ketonitriles like (XI) and
(XIII). — (HERNANDEZ, R.; LEON, E. I.; MORENO, P.; RIESCO-FAGUNDO, C.;
SUAREZ*, E.; J. Org. Chem. 69 (2004) 24, 8437-8444; Inst. Prod. Nat. Agrobiol.,
CSIC, Univ. La Laguna, E-38206 La Laguna, Tenerife, Spain; Eng.) — Jannicke
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