Alternative route to the diisocyanate building block 1,4-Diisocyanato-4- Methylpentane (DIMP)
The synthesis of 1,4-diisocyanato-4-methylpentane was accomplished starting from isobutyronitrile in six steps with 53% overall yield. The two isocyanates were installed by a double Curtius rearrangement. The product reacts with alcohol in a regioselective manner. Copyright Taylor & Francis Group, LLC.
Catalytic asymmetric synthesis of a tertiary benzylic carbon center via phenol-directed alkene hydrogenation
An expeditious synthetic approach to chiral phenol 1, a key building block in the preparation of a series of drug candidates, is reported. The strategy includes a cost-effective and readily scalable route to cyclopentanone 3 from isobutyronitrile (10). The sterically hindered and enolizable ketone 3 was subsequently employed in a challenging Grignard addition mediated by LaCl 3?2LiCl. A novel preparation of the lanthanide reagent required for this transformation is described. To complete the process, a highly enantioselective hydrogenation step afforded the target (1). The importance of the phenol group to the success of this asymmetric transformation is discussed.
Caille, Seb,Crockett, Rich,Ranganathan, Krishnakumar,Wang, Xiang,Woo, Jacqueline C. S.,Walker, Shawn D.
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p. 5198 - 5206
(2011/08/09)
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