Diastereotopic group selectivity at a prostereogenic carbon center: Synthesis of (±)-syn-4, 8-dimethyldecanal
SL Schreiber, B Hulin
Index: Schreiber, Stuart L.; Hulin, Bernard Tetrahedron Letters, 1986 , vol. 27, # 38 p. 4561 - 4564
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Citation Number: 17
Abstract
Abstract A group selective dealkylation reaction of a bridged ketal with trimethylsilyl iodide serves to control stereochemistry at carbon centers that are separated by five atoms. In combination with the iron/copper promoted fragmentation reaction of a hydroperoxide, a new synthesis of (±)-syn-4, 8-dimethyldecanal has been achieved.
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[Iwata, Chuzo; Fujita, Masahiro; Moritani, Yasunori; Sugiyama, Kenji; Hattori, Kohji; Imanishi, Takeshi Tetrahedron Letters, 1987 , vol. 28, # 27 p. 3131 - 3134]
[Iwata, Chuzo; Fujita, Masahiro; Moritani, Yasunori; Sugiyama, Kenji; Hattori, Kohji; Imanishi, Takeshi Tetrahedron Letters, 1987 , vol. 28, # 27 p. 3131 - 3134]