anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst.

anti-selective direct asymmetric Mannich reactions catalyzed by axially chiral amino sulfonamide as an organocatalyst.
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DOI:
10.1021/ja056008w
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发表时间:
2005-11
影响因子:
15
通讯作者:
T. Kano;Yukako Yamaguchi;Osamu Tokuda;K. Maruoka
T. Kano;Yukako Yamaguchi;Osamu Tokuda;K. Maruoka
中科院分区:
化学1区
文献类型:
--
作者:
T. Kano;Yukako Yamaguchi;Osamu Tokuda;K. Maruoka

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利用一种新型的轴手性氨基三氟甲磺酰胺(S)-3,以高反选择性和对映选择性的方式,发展了一种直接的不对称Mannich反应。因此,在催化量的(S)-3存在下,醛和α-亚氨基酯4之间的反应顺利进行,得到具有比以前可能的显著更高的反式/顺式比率和对映选择性的官能化β-氨基醛。
A direct asymmetric Mannich reaction using a novel axially chiral amino trifluoromethanesulfonamide (S)-3 has been developed in highly anti-selective and enantioselective manners. Thus, in the presence of a catalytic amount of (S)-3, the reactions between aldehydes and the alpha-imino ester 4 proceed smoothly to give the functional beta-amino aldehydes with significantly higher anti/syn ratio and enantioselectivity than previously possible.