Asymmetric Addition of Alkynylzinc Reagents to Nitrones Utilizing Tartaric Acid Ester as a Chiral Auxiliary
Asymmetric Addition of Alkynylzinc Reagents to Nitrones Utilizing Tartaric Acid Ester as a Chiral Auxiliary
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DOI：
10.1246/cl.2006.176
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发表时间：
2006-01
影响因子：
1.6
通讯作者：
Weilin Wei;Masato Kobayashi;Y. Ukaji;K. Inomata
中科院分区：
文献类型：
--
作者：
Weilin Wei;Masato Kobayashi;Y. Ukaji;K. Inomata
以酒石酸二(叔丁基)(R，R)-酒石酸酯为手性助剂，合成了具有光学活性的(R)-α取代的丙叉羟胺，实现了由二烷基锌和1-炔基原位合成的炔基锌试剂与硝酮的不对称加成反应。通过添加类似产物的N-羟胺，观察到了前所未有的对映选择性的提高，使N-羟胺的对映选择性高达95%ee。
The asymmetric addition of alkynylzinc reagents, prepared in situ from dialkylzinc and 1-alkynes, to nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (R)-α-substituted propargylic N-hydroxylamines. By the addition of product-like N-hydroxylamine, unprecedented enhancement of enantioselectivity was observed to afford the N-hydroxylamines up to 95% ee.