Synthesis of pyrroloindolines through formal [3+2]-cycloaddition of indoles with chiral N-2-acetamidoacrylyl oxazolidinones

被引：2
|
作者：
Smith, Isaac T. [1 ]
Neeley, Jared B. [1 ]
Brinley, Tanner D. [1 ]
Fullmer, Peter R. [1 ]
Andrus, Merritt B. [1 ]
机构：
[1] Brigham Young Univ, Dept Chem & Biochem, C100 BNSN, Provo, UT 84602 USA
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 23期
关键词：
Pyrroloindoline; Oxazolidinone; 3,2]-Cycloaddition; Tin(IV) chloride; ENANTIOSELECTIVE SYNTHESIS; 3+2 CYCLOADDITION; CONCISE SYNTHESIS; CONSTRUCTION; CYCLIZATION; AMAUROMINE; STRATEGY; NOCARDIOAZINES; TRYPTAMINES; AUXILIARIES;
D O I：
10.1016/j.tetlet.2020.151947
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral N-2-acetamidoacrylyl oxazolidinones were produced and reacted with indoles under Lewis acid conditions to generate hexahydropyrrolo[2,3-b]indole products in a formal [3 + 2] cycloaddition process. Optimal conditions included the use of tin(IV) chloride in methylene chloride at 0 degrees C. Pyrroloindoline products were obtained from various indoles with shorter reaction times (12 hr) up to 91% yield with high, >20:1 exo selectivity. A mechanism involving reversible conjugate addition followed by an enamine lone-pair-iminium capture, tautomerization, and tin-enolate protonation accounts for the selectivity. The method enables selective applications to pyrroloindoline targets and further refinement with chiral catalysts. (C) 2020 Elsevier Ltd. All rights reserved.
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页数：5
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