Photochemically Produced Aminocyclobutanes as Masked Dienes in Thermal Electrocyclic Cascade Reactions

被引：16

作者：

Elliott, Luke D. ^{[1
]}

Booker-Milburn, Kevin I. ^{[1
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

FLOW REACTOR; IMIDE SYSTEM; CYCLOBUTENES; ACID;

D O I：

10.1021/acs.orglett.9b00211

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclobutane products of a triplet sensitized enamide-alkene intramolecular [2 + 2] photocycloaddition have been shown to undergo fragmentation under acidic conditions. This lability has been exploited by inducing a complexity-generating thermal electrocyclic cascade sequence involving the in situ formation of a cyclobutene, followed by electrocyclic ring opening, Diels-Alder cycloaddition, and subsequent lactamization. This combination of excited state photochemistry and thermal electrocyclic cascade reactions allows simple planar molecules to be rapidly transformed into sp(3)-rich scaffolds.

引用

页码：1463 / 1466

页数：4

共 40 条

[1] 2,3-BIS(TRIMETHYLSILYLOXY)-1,3-BUTADIENE AS A USEFUL REACTIVE DIENE IN DIELS-ALDER REACTION [J].

ANDERSON, DR ;

KOCH, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (13) :2726-2728

[2] Photochemical Reactions as Key Steps in Natural Product Synthesis [J].

Bach, Thorsten ;

Hehn, Joerg P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1000-1045

[3] THERMAL ELECTROCYCLIC RING-OPENING OF CYCLOBUTENES - STEREOSELECTIVE ROUTES TO FUNCTIONALIZED CONJUGATED (Z,E)-DIENES AND (E,E)-2,4-DIENALS [J].

BINNS, F ;

HAYES, R ;

INGHAM, S ;

SAENGCHANTARA, ST ;

TURNER, RW ;

WALLACE, TW .

TETRAHEDRON, 1992, 48 (03) :515-530

[4] Sequential ring-opening/cyclisation reactions of bicyclo[4.2.0]oct-7-enes for the synthesis of cyclooctadiene fused lactones:: Model studies towards the total synthesis of pachylactone [J].

Booker-Milburn, KI ;

Jiménez, FD ;

Sharpe, A .

TETRAHEDRON, 1999, 55 (18) :5889-5902

[5] Preparation of Cyclobutene Acetals and Tricyclic Oxetanes through Photochemical Tandem and Cascade Reactions [J].

Buendia, Julien ;

Chang, Zong ;

Eijsberg, Hendrik ;

Guillot, Regis ;

Frongia, Angelo ;

Secci, Francesco ;

Xie, Juan ;

Robin, Sylvie ;

Boddaert, Thomas ;

Aitken, David J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) :6592-6596

[6] Building C(sp3)-rich complexity by combining cycloaddition and C-C cross-coupling reactions [J].

Chen, Tie-Gen ;

Barton, Lisa M. ;

Lin, Yutong ;

Tsien, Jet ;

Kossler, David ;

Bastida, Inaki ;

Asai, Shota ;

Bi, Cheng ;

Chen, Jason S. ;

Shan, Mingde ;

Fang, Hui ;

Fang, Francis G. ;

Choi, Hyeong-Wook ;

Hawkins, Lynn ;

Qin, Tian ;

Baran, Phil S. .

NATURE, 2018, 560 (7718) :350-+

[7] PHOTOCHEMISTRY OF CIS-1-PHENYLCYCLOHEXENE - PROOF OF INVOLVEMENT OF TRANS ISOMER IN REACTION PROCESSES [J].

DAUBEN, WG ;

VANRIEL, HCHA ;

ROBBINS, JD ;

WAGNER, GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (21) :6383-6389

[8] Visible Light Mediated Generation of trans-Arylcyclohexenes and Their Utilization in the Synthesis of Cyclic Bridged Ethers [J].

Day, Jon I. ;

Singh, Kamaljeet ;

Trinh, Winston ;

Weaver, Jimmie D., III .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (31) :9934-9941

[9] Photochemical Synthesis of 2-Azabicyclo[3.2.0]heptanes: Advanced Building Blocks for Drug Discovery. Synthesis of 2,3-Ethanoproline [J].

Druzhenko, Tetiana ;

Skalenko, Yevhen ;

Samoilenko, Maryna ;

Denisenko, Aleksandr ;

Zozulya, Sergey ;

Borysko, Petro O. ;

Sokolenko, Maria I. ;

Tarasov, Alexandr ;

Mykhailiuk, Pavel K. .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03) :1394-1401

[10] Using batch reactor results to calculate optimal flow rates for the scale-up of UV photochemical reactions [J].

Elliott, L. D. ;

Knowles, J. P. ;

Stacey, C. S. ;

Klauber, D. J. ;

Booker-Milburn, K. I. .

REACTION CHEMISTRY & ENGINEERING, 2018, 3 (01) :86-93

← 1 2 3 4 →