Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.

Enantioselective synthesis of pyrroloindolines by a formal [3 + 2] cycloaddition reaction.
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DOI:
10.1021/ja107328g
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发表时间:
2010-10-20
影响因子:
15
通讯作者:
Reisman SE
Reisman SE
中科院分区:
化学1区
文献类型:
--
作者:
Repka LM;Ni J;Reisman SE

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(R)-BINOL·SnCl_4催化C(3)-取代吲哚与2-酰胺基丙烯酸酯的[3+2]环加成反应生成吡咯并吲哚啉。以简单的前体为原料,一步合成了多种对映选择性高的吡咯并吲哚啉。这种方法有望促进吡咯并吲哚啉生物碱,一类重要的生物活性天然产物的全合成。
(R)-BINOL•SnCl4 was found to catalyze a formal [3+2] cycloaddition reaction between C(3)-substituted indoles and 2-amidoacrylates to provide pyrroloindolines. A variety of pyrroloindolines were prepared with high enantioselectivity in one step from simple precursors. This methodology is expected to facilitate the total synthesis of pyrroloindoline alkaloids, an important class of biologically active natural products.
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