Citation:
Li Yan, Huang Jinxia, Ma Xingquan, Chen Zuxing, Xu Zhanghuang. Synthesis of (3R,4R)-4-Methyl-3-heptanol[J]. Chinese Journal of Applied Chemistry,
;1999, 16(2): 76-78.
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(3R,4R)-4-Methyl-3-heptanol, the enatiomer of aggregation pheromone of the smaller European elm bark beetle (Scolytus Multistrialus), was stereoselectively synthesized using N-bornane-2,10-sultam as a chiral auxiliary. The two asymmetric carbon atoms of the target product were achieved by employing asymmetric syn-aldolization of N-propionylbornane-2,10-sultam (3) with propylaldehyde. The enantiomeric excess of (3R,4R)-4-methyl-3-heptanol prepared by this route is about 94.3%.
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