Chiral Bronsted Base-Promoted Nitroalkane Alkylation: Enantioselective Synthesis of sec-Alkyl-3-Substituted Indoles

被引：71
作者：
Dobish, Mark C.
Johnston, Jeffrey N. [1 ]
机构：
[1] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA
来源：
ORGANIC LETTERS | 2010年 / 12卷 / 24期
关键词：
FRIEDEL-CRAFTS ALKYLATION; FORMAL TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; ARYLSULFONYL INDOLES; SPIROTRYPROSTATIN-B; 3-(1-ARYLSULFONYLALKYL) INDOLES; PROTON CATALYSIS; NITRO-OLEFINS; IN-SITU; DERIVATIVES;
D O I：
10.1021/ol1025712
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A Bronsted base-catalyzed reaction of nitroalkanes with alkyl electrophiles provides indole heterocycles substituted at C3 bearing a sec-alkyl group with good enantioselectivity (up to 90% ee). Denitration by hydrogenolysis provides a product with equally high ee. An indolenine intermediate is implicated in the addition step, and surprisingly, water cosolvent was found to have a beneficial effect in this step, leading to a one-pot protocol for elimination/enantioselective addition using PBAM, a bis(amidine) chiral nonracemic base.
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收藏
页码：5744 / 5747
页数：4
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