GaCl3-Catalyzed Ring-Opening Carbonyl-Olefin Metathesis

被引:48
作者
Albright, Haley [1 ]
Vonesh, Hannah L. [1 ]
Becker, Marc R. [1 ]
Alexander, Brandon W. [1 ]
Ludwig, Jacob R. [1 ]
Wiscons, Ren A. [1 ]
Schindler, Corinna S. [1 ]
机构
[1] Univ Michigan, Dept Chem, Willard Henry Dow Lab, 930 North Univ Ave, Ann Arbor, MI 48109 USA
基金
美国国家科学基金会;
关键词
CROSS-METATHESIS; PHOTOPROTOLYTIC OXAMETATHESIS; CATALYZED OLEFINATION; STRAIN; HYDROCARBONS; STEP;
D O I
10.1021/acs.orglett.8b02086
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of a Lewis acid-catalyzed ring-opening cross-metathesis reaction which enables selective access to acyclic, unsaturated ketones as the carbonyl olefin metathesis products is described. While catalytic amounts of FeCl3 were previously identified as optimal to catalyze ring dosing metathesis reactions, the complementary ring-opening metathesis between cyclic alkenes and carbonyl functionalities relies on GaCl3 as the superior Lewis acid catalyst.
引用
收藏
页码:4954 / 4958
页数:5
相关论文
共 39 条
[21]   Iron(III)-catalysed carbonyl-olefin metathesis [J].
Ludwig, Jacob R. ;
Zimmerman, Paul M. ;
Gianino, Joseph B. ;
Schindler, Corinna S. .
NATURE, 2016, 533 (7603) :374-379
[22]   FeCl3-Catalyzed Ring-Closing Carbonyl-Olefin Metathesis [J].
Ma, Lina ;
Li, Wenjuan ;
Xi, Hui ;
Bai, Xiaohui ;
Ma, Enlu ;
Yan, Xiaoyu ;
Li, Zhiping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) :10410-10413
[23]   Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis [J].
McAtee, Christopher C. ;
Riehl, Paul S. ;
Schindler, Corinna S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (08) :2960-2963
[24]   Selective ring opening cross metathesis of cyclopropenone ketal: a one step synthesis of protected divinyl ketones [J].
Michaut, M ;
Parrain, JL ;
Santelli, M .
CHEMICAL COMMUNICATIONS, 1998, (23) :2567-2568
[25]   Selective ring opening cross metathesis of cyclooctadiene and trisubstituted cycloolefins [J].
Morgan, JP ;
Morrill, C ;
Grubbs, RH .
ORGANIC LETTERS, 2002, 4 (01) :67-70
[26]   Direct Organocatalytic Oxo-Metathesis, a trans-Selective Carbocation-Catalyzed Olefination of Aldehydes [J].
Naidu, Veluru Ramesh ;
Bah, Juho ;
Franzen, Johan .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (08) :1834-1839
[27]   An efficient carbonyl-alkene metathesis of bicyclic oxetanes:: photoinduced electron transfer reduction of the Paterno-Buchi adducts from 2,3-dihydrofuran and aromatic aldehydes [J].
Pérez-Ruiz, R ;
Miranda, MA ;
Alle, R ;
Meerholz, K ;
Griesbeck, AG .
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2006, 5 (01) :51-55
[28]   Stereodifferentiation in the photochemical cycloreversion of diastereomeric methoxynaphthalene-oxetane dyads [J].
Pérez-Ruiz, R ;
Gil, S ;
Miranda, MA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1376-1381
[29]   EVALUATION OF STRAIN IN HYDROCARBONS - STRAIN IN ADAMANTANE AND ITS ORIGIN [J].
SCHLEYER, PV ;
WILLIAMS, JE ;
BLANCHARD, KR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (08) :2377-+
[30]  
SCHOPOV I, 1983, MAKROMOL CHEM-RAPID, V4, P659