芳基铜试剂与手性亚磺酰基取代的吡咯基α,β-不饱和酰胺进行共轭加成反应过程中的1,6-不对称诱导作用。
1,6-Asymmetric induction during the conjugate addition of arylcopper reagents to a chiral sulfinyl-substituted pyrrolyl alpha,beta-unsaturated amide.
作者信息
Arai Y, Ueda K, Xie J, Masaki Y
机构信息
Gifu Pharmaceutical University, Japan.
出版信息
Chem Pharm Bull (Tokyo). 2001 Dec;49(12):1609-14. doi: 10.1248/cpb.49.1609.
The asymmetric conjugate addition of arylcopper reagents derived from aryl Grignard reagents and copper(I) iodide to a chiral 1-[2-(p-tolylsulfinyl)]pyrrolyl cinnamide proceeded smoothly to give (3R)-adducts with high diastereoselectivities (> or =92% de) in high yields. Conjugate additions either of the cinnamide with the alkyl Grignard reagent-copper(l) iodide combination or of the crotonamide derivative with aryl Grignard reagent-copper(l) iodide gave moderate to good diastereoselectivities. With these sulfinyl pyrrolyl alpha,beta-unsaturated amides, the chiral auxiliary was efficiently recovered without any loss of optical purity after asymmetric conjugate addition.
由芳基格氏试剂和碘化亚铜衍生的芳基铜试剂与手性1-[2-(对甲苯基亚磺酰基)]吡咯基肉桂酰胺的不对称共轭加成反应顺利进行，以高产率得到非对映选择性高（非对映体过量≥92%）的(3R)-加合物。肉桂酰胺与烷基格氏试剂-碘化亚铜组合或巴豆酰胺衍生物与芳基格氏试剂-碘化亚铜的共轭加成反应给出中等至良好的非对映选择性。对于这些亚磺酰基吡咯基α,β-不饱和酰胺，在不对称共轭加成后，手性助剂能够有效地回收，且光学纯度没有任何损失。
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