| Title: | "Efficient and stereoselective synthesis of yellow scale pheromone via alkyne haloboration, Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction), and Pd-catalyzed tandem Negishi coupling" |
| Address: | "Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA. negishi@purdue.edu" |
| ISSN/ISBN: | 1523-7052 (Electronic) 1523-7060 (Print) 1523-7052 (Linking) |
| Abstract: | A Pd-catalyzed reaction of allylzincs with the 1-octyne bromoboration product gives the desired allyl-alkenyl coupling products in good yields except with H 2CCHCH 2ZnBr. This reaction is suitable for converting an alkyne bromoboration product 3 into 4 with no isomerization or beta-elimination. The Pd-catalyzed isoalkyl-alkenyl coupling of 4 with the isoalkylzinc reagent derived from 2 provides yellow scale pheromone ( 1) of >/=98% isomeric purity in 34% in six steps from TBDPS-protected homoallyl alcohol |
| Keywords: | Alkenes/*chemistry Alkynes/*chemistry Catalysis Palladium/*chemistry Pheromones/*chemical synthesis/chemistry Stereoisomerism Substrate Specificity Zirconium/*chemistry; |
| Notes: | "MedlineXu, Zhaoqing Negishi, Ei-Ichi eng R01 GM036792/GM/NIGMS NIH HHS/ R01 GM036792-21/GM/NIGMS NIH HHS/ GM 36792/GM/NIGMS NIH HHS/ Research Support, N.I.H., Extramural Research Support, Non-U.S. Gov't 2008/09/04 Org Lett. 2008 Oct 2; 10(19):4311-4. doi: 10.1021/ol8017566. Epub 2008 Sep 3" |
