Acetic acid promoted tandem cyclization of in situ generated 1,3-dipoles: stereoselective synthesis of dispiroimidazolidinyl and dispiropyrrolidinyl oxindoles with multiple chiral stereocenters

Suman Koorathota; Thennarasu Sathiah

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Acetic acid promoted tandem cyclization of in situ generated 1,3-dipoles: stereoselective synthesis of dispiroimidazolidinyl and dispiropyrrolidinyl oxindoles with multiple chiral stereocenters

机译：乙酸促进原位生成的1,3-偶极的串联环化：具有多个手性立体中心的dispiroimidazolidinyl和dispiropyrrolidinyl羟吲哚的立体选择性合成

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We report acetic acid promoted in situ generation of ketimine and a 1,3-dipole that results in regio- and diastereoselective formation of dispiropyrrolidineoxindoles and dispiroimidazolidineoxindoles via tandem cycloaddition. This novel one-pot reaction generates four chiral centres with two contiguous spirostereocenters in dispiropyrrolidineoxindoles, and three chiral centres with two distal spirostereocenters in dispiroimidazolidineoxindoles.

机译：我们报道了乙酸促进的ketimine和1,3-偶极的原位生成，通过串联环加成反应导致dispiropyrrolidineoxindoles和dispiroimidazolidineoxindoles的区域和非对映选择性形成。这一新颖的一锅式反应在双螺吡咯烷并吲哚中产生四个手性中心，其中两个连续的螺甾体中心，而在双螺并咪唑并恶臭中生成三个手性中心，并具有两个远端的螺甾体中心。

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《RSC Advances》 |2015年第97期|共10页
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Suman Koorathota; Thennarasu Sathiah;
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中图分类化学;
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1. Acetic acid promoted tandem cyclization of in situ generated 1,3-dipoles: stereoselective synthesis of dispiroimidazolidinyl and dispiropyrrolidinyl oxindoles with multiple chiral stereocenters [J] . Suman Koorathota, Thennarasu Sathiah RSC Advances . 2015,第97期

机译：乙酸促进原位生成的1,3-偶极的串联环化：具有多个手性立体中心的dispiroimidazolidinyl和dispiropyrrolidinyl羟吲哚的立体选择性合成
2. One-Pot Synthesis of Enantiopure Spiro[3,4-dihydrobenzo[b][1,4]oxazine-2,3 '-oxindole] via Regio- and Stereoselective Tandem Ring Opening/Cyclization of Spiroaziridine Oxindoles with Bromophenols [J] . Hajra Saumen, Hazra Atanu, Abu Saleh S. K. The Journal of Organic Chemistry . 2019,第16期

机译：通过Regio-and StereoSelective Tandem环开/环化的苯磺酸串环开/环化苯磺酸盐串联/环丁香的单位合成苯磺酸[3,4-二氢苯并[B] [B] [B] [1,4] - 二氧化氮吲哚，用溴噻烯酚
3. Practical way for the synthesis of 4H-benzo[e][1,3]oxazine by anhydride-promoted [4+2] cyclization of in situ generated o-quinone methides with amides [J] . Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2020,第23期

机译：通过酸酐促进的4H-苯并[e] [1,3]恶嗪合成4H-苯并[1,3]的实际方法，原位产生的o-醌氨基氨基化与酰胺
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机译：I. A1,3-菌株能够在β-酮基酰胺的双环化过程中保留手性：salinosporamide a和衍生物II的不对称合成和生物活性。有机合成程序的优化：醛酸不对称亲核催化醛醇内酯化
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6. One-Pot Synthesis of Enantiopure Spiro3,4-dihydrobenzob1,4oxazine-2,3-oxindole via Regio- and Stereoselective Tandem Ring Opening/Cyclization of Spiroaziridine Oxindoles with Bromophenols [O] . -1

机译：通过Regio和立体选择串联环开口/环化与苯磺烯醇酸丁基氧胆砂的串联环开口/环化的单壶合成苯磺酸3,4-二氢苯并B B B 1,4 B 1,4 1,4 1,4

Acetic acid promoted tandem cyclization of in situ generated 1,3-dipoles: stereoselective synthesis of dispiroimidazolidinyl and dispiropyrrolidinyl oxindoles with multiple chiral stereocenters

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