Enantioselective 1,3-dipolar cycloaddition reaction between diazoacetates and α-substituted acroleins:: Total synthesis of manzacidin A
Enantioselective 1,3-dipolar cycloaddition reaction between diazoacetates and α-substituted acroleins:: Total synthesis of manzacidin A
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DOI：
10.1021/ja056851u
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发表时间：
2006-02-22
影响因子：
15
通讯作者：
Maruoka, K
中科院分区：
文献类型：
--
作者：
Kano, T;Hashimoto, T;Maruoka, K
研究了BINOLate钛催化的α-取代丙烯醛与重氮乙酸烷基酯的不对称1，3-偶极环加成反应。用这种方法在手，手性2-吡唑啉含有一个四元立体中心，得到了高至优异的对映选择性（高达95%ee）。由此获得的光学富集的2-吡唑啉的合成效用在短的杀Manzacidin A的合成中得到证实。
A titanium BINOLate catalyzed asymmetric 1,3-dipolar cycloaddition reaction between α-substituted acroleins and alkyl diazoacetates has been developed. With this methodology in hand, chiral 2-pyrazolines containing a quaternary stereogenic center were obtained in high to excellent enantioselectivities (up to 95% ee). The synthetic utility of the optically enriched 2-pyrazoline thus obtained was demonstrated in the short synthesis of manzacidin A.