Asymmetric organocatalytic synthesis of cis-substituted dihydrobenzofuranols via intramolecular aldol reactions

被引:46
作者
Enders, Dieter
Niemeier, Oliver
Straver, Leo
机构
[1] Univ Aachen, Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
[2] Bruker AXS BV, Applicat SCD, NL-2600 AV Delft, Netherlands
关键词
organocatalysis; aldol reaction; asymmetric synthesis; proline; dihydrobenzofuran;
D O I
10.1055/s-2006-956454
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The diastereo- and enantioselective synthesis of 3-hydroxy 2.3-dihydrobenzofurans via an intramolecular cis-selective aldol reaction employing proline-type organocatalysts is described enabling a new entry to coumarine natural products.
引用
收藏
页码:3399 / 3402
页数:4
相关论文
共 56 条
[1]   Coumarins from Opopanax chironium.: New dihydrofuranocoumarins and differential induction of apoptosis by imperatorin and heraclenin [J].
Appendino, G ;
Bianchi, F ;
Bader, A ;
Campagnuolo, C ;
Fattorusso, E ;
Taglialatela-Scafati, O ;
Blanco-Molina, M ;
Macho, A ;
Fiebich, BL ;
Bremner, P ;
Heinrich, M ;
Ballero, M ;
Muñoz, E .
JOURNAL OF NATURAL PRODUCTS, 2004, 67 (04) :532-536
[2]   Quantum mechanical predictions of the stereoselectivities of proline-catalyzed asymmetric intermolecular aldol reactions [J].
Bahmanyar, S ;
Houk, KN ;
Martin, HJ ;
List, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (09) :2475-2479
[3]   The origin of stereoselectivity in proline-catalyzed intramolecular aldol reactions [J].
Bahmanyar, S ;
Houk, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (51) :12911-12912
[4]   Transition states of amine-catalyzed aldol reactions involving enamine intermediates: Theoretical studies of mechanism, reactivity, and stereoselectivity [J].
Bahmanyar, S ;
Houk, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (45) :11273-11283
[5]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[6]   New developments in the asymmetric Stetter reaction [J].
Christmann, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (18) :2632-2634
[7]   ASYMMETRIC INDUCTION IN 19-NORSTEROID TOTAL SYNTHESIS [J].
COHEN, N .
ACCOUNTS OF CHEMICAL RESEARCH, 1976, 9 (11) :412-417
[8]   Proline-catalyzed one-step asymmetric synthesis of 5-hydroxy-(2E)-hexenal from acetaldehyde [J].
Córdova, A ;
Notz, W ;
Barbas, CF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :301-303
[9]  
Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
[10]  
2-D