Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
Asymmetric synthesis of protected arylglycines by rhodium-catalyzed addition of arylboronic acids to N-tert-butanesulfinyl imino esters
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DOI：
10.1021/ja060529h
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发表时间：
2006-05-17
影响因子：
15
通讯作者：
Ellman, Jonathan A.
中科院分区：
文献类型：
--
作者：
Beenen, Melissa A.;Weix, Daniel J.;Ellman, Jonathan A.
提出了一种新的Rh(I)催化芳基硼酸对叔丁基磺酰亚胺酯的加成反应方法，用于芳基甘氨酸衍生物的不对称合成。该方法为各种官能化的芳基硼酸提供了高的产率(61−90%)和非对映选择性(>；98：2)。然后，亚磺酰芳基甘氨酸酯产品是用于进一步转化的多种中间体，包括选择性地去除保护基团，转化为β-氨基醇，以及直接掺入多肽。
A new method for the Rh(I)-catalyzed addition of arylboronic acids toN-tert-butanesulfinyl imino esters has been developed for the asymmetric synthesis of arylglycine derivatives. This method provides high yields (61−90%) and diastereoselectivities (>98:2) for a variety of functionalized arylboronic acids. TheN-sulfinyl arylglycine ester products are versatile intermediates for further transformations, including selective protecting group removal, conversion to β-amino alcohols, and direct incorporation into peptides.