Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (-)-fenchone skeleton
Highly effective and practical stereoselective synthesis of new homoallylic alcohols with (+)-camphor and (-)-fenchone skeleton
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DOI：
10.1016/0040-4020(95)01005-x
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发表时间：
1996-01-29
期刊：
影响因子：
2.1
通讯作者：
Kostova, K
中科院分区：
文献类型：
--
作者：
Dimitrov, V;Simova, S;Kostova, K
通过3-5-取代烯丙基格氏试剂3-5与1和2的立体选择性加成反应，高产率地合成了含(1R)(+)-樟脑(1)的手性非外消旋高烯丙基外醇6，7，10和具有(1R)-(-)-芳香酮(2)骨架的内醇8，9，11。2-丁烯基(巴豆基)试剂5高选择性地加成了α-甲基烯丙醇10与酮1和(Z)-2-丁烯醇11与酮2。用核磁共振方法确定了高烯丙醇的绝对构型。
The new chiral nonracemic homoallylic exo-alcohols 6, 7, 10 with (1R)(+)-camphor (1) and endo-alcohols 8, 9, 11 with (1R)-(-)-fenchone (2) skeleton were synthesized in high yields by the stereoselective addition of allyl and substituted allylic Grignard reagents 3-5 to 1 and 2, respectively. The addition of the 2-butenyl (crotyl) reagent 5 occurred with high selectivity leading exclusively to alpha-methylallyl alcohol 10 with ketone 1 and to (Z)-2-butenyl alcohol 11 with ketone 2. The absolute configurations of the homoallylic alcohols 6-11 were determined by NMR methods.