Industrial Applications of the Diels-Alder Reaction

被引:240
作者
Funel, Jacques-Alexis [1 ]
Abele, Stefan [1 ]
机构
[1] Actel Pharmaceut Ltd, Proc Res Chem, CH-4123 Allschwil, Switzerland
关键词
cycloaddition; DielsAlder reaction; industrial chemistry; process chemistry; synthetic methods; RESEARCH-AND-DEVELOPMENT; GAMMA-SECRETASE INHIBITORS; VITAMIN-D ANALOGS; ENANTIOSELECTIVE SYNTHESIS; KEY INTERMEDIATE; LARGE-SCALE; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; RECEPTOR ANTAGONIST; EFFICIENT SYNTHESIS;
D O I
10.1002/anie.201201636
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The DielsAlder reaction is one of the most popular transformations for organic chemists to generate molecular complexity efficiently. Surprisingly, little is known about its industrial application for the synthesis of pharmacologically active ingredients, agrochemicals, and flavors and fragrances. This Review highlights selected examples, with a focus on large-scale applications (>1kg) from a process research and development perspective.
引用
收藏
页码:3822 / 3863
页数:42
相关论文
共 379 条
[1]  
Abdel-Magid A. F., 2001, [No title captured], Patent No. [WO2001000571A1, 200100057]
[2]   Safety Assessment of Diels-Alder Reactions with Highly Reactive Acrylic Monomers [J].
Abele, Stefan ;
Schwaninger, Mischa ;
Fierz, Hans ;
Schmidt, Gunther ;
Funel, Jacques-Alexis ;
Stoessel, Francis .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (12) :2015-2020
[3]   High-Temperature Diels-Alder Reactions: Transfer from Batch to Continuous Mode [J].
Abele, Stefan ;
Hoeck, Stefan ;
Schmidt, Gunther ;
Funel, Jacques-Alexis ;
Marti, Roger .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (05) :1114-1120
[4]   Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands [J].
Abele, Stefan ;
Inauen, Roman ;
Spielvogel, Dirk ;
Moessner, Christian .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (10) :4765-4773
[5]   Design and Scale-Up of a Practical Enantioselective Route to 5-Phenylbicyclo[2.2.2]oct-5-en-2-one [J].
Abele, Stefan ;
Inauen, Roman ;
Funel, Jacques-Alexis ;
Weller, Thomas .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (01) :129-140
[6]   DIASTEREOSELECTIVE AZA-DIELS-ALDER REACTION - USE OF 1-PHENYLETHYLIMINE OF ALKYL GLYOXYLATE FOR SYNTHESIS OF CYCLIC ALPHA-AMINO-ACIDS [J].
ABRAHAM, H ;
STELLA, L .
TETRAHEDRON, 1992, 48 (44) :9707-9718
[7]   The synthetic development of the anti-influenza neuraminidase inhibitor oseltamivir phosphate (Tamiflu®):: A challenge for synthesis & process research [J].
Abrecht, S ;
Harrington, P ;
Iding, H ;
Karpf, M ;
Trussardi, R ;
Wirz, B ;
Zutter, U .
CHIMIA, 2004, 58 (09) :621-629
[8]  
Abrecht S., 2001, Patent No. 1127872
[9]   Putting chirality to work: The strategy of chiral switches [J].
Agranat, I ;
Caner, H ;
Caldwell, A .
NATURE REVIEWS DRUG DISCOVERY, 2002, 1 (10) :753-768
[10]   Information on diene synthesis, II Announcement - Concerning the thermal breakdown of addition products of acetylene-dicarbonic esters [J].
Alder, K ;
Rickert, HF .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1937, 70 :1354-1363