1,4-Asymmetric induction in the titanium-mediated aldol reactions of α-benzyloxy methyl ketones

被引：16

作者：

Pellicena, Miquel ^{[1
]}

Solsona, Joan G. ^{[1
]}

Romea, Pedro ^{[1
]}

Urpi, Felix ^{[1
]}

机构：

[1] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Catalonia, Spain

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 36期

关键词：

stereoselective reactions; acetate aldol reactions; titanium enolates; chiral ketones;

D O I：

10.1016/j.tetlet.2008.06.120

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Good levels of 1,4-anti asymmetric induction are obtained in the TiCl(3)(i-PrO)-mediated aldol reaction of alpha-benzyloxy methyl ketones with achiral alclehydes. Such methodology represents a new approach to the substrate-controlled acetate aldol reaction, which can be Useful to design more efficient synthesis. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5265 / 5267

页数：3

共 50 条

[41] ENANTIOSPECIFIC TOTAL SYNTHESIS OF (-)-MEGAPHONE BY A HIGHLY CONTROLLED CONSECUTIVE 1,4-ASYMMETRIC AND 1,3-ASYMMETRIC INDUCTION
TOMIOKA, K
KAWASAKI, H
IITAKA, Y
KOGA, K
TETRAHEDRON LETTERS, 1985, 26 (07) : 903 - 906
[42] Investigations on 1,2-, 1,3-, and 1,4-asymmetric induction in intramolecular reformatsky reactions promoted by samarium(II) iodide
1600, (113):
[43] EFFICIENT 1,4-ASYMMETRIC INDUCTION UTILIZING ELECTROSTATIC INTERACTION BETWEEN LIGAND AND SUBSTRATE IN THE ASYMMETRIC HYDROGENATION OF DIDEHYDRODIPEPTIDES
YAMAGISHI, T
IKEDA, S
YATAGAI, M
YAMAGUCHI, M
HIDA, M
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07): : 1787 - 1790
[44] 1,4-asymmetric induction from chiral delta-oxygenated allylic tin reagents
Nishigaichi, Y
Yoshikawa, M
Takigawa, Y
Takuwa, A
CHEMISTRY LETTERS, 1996, (11) : 961 - 962
[45] Formal Total Synthesis of Fostriecin by 1,4-Asymmetric Induction with an Alkyne-Cobalt Complex
Hayashi, Yujiro
Yamaguchi, Hirofumi
Toyoshima, Maya
Okado, Kotaro
Toyo, Takumi
Shoji, Mitsuru
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) : 10150 - 10159
[46] 1,4-Induction in aldol reactions of (tertiary α′-alkoxy)methyl ketones: synthesis of the C8-C11 stereotriad of ent-fostriecin
Cowper, Nicholas
Azzi, Soula
Dupont-Gaudet, Kristina
Burch, Jason D.
TETRAHEDRON LETTERS, 2012, 53 (14) : 1837 - 1839
[47] Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of -Haloketones
Le, Nathan N.
Rodriguez, Aimee M.
Alleyn, James R.
Gesinski, Michael R.
SYNLETT, 2018, 29 (16) : 2195 - 2198
[48] An Alternative Mechanism for the 1,4-Asymmetric Induction in the Stereoselective Addition of (R)-Pantolactone to 2-Phenylpropylketene
Silva, Alexander M.
da Silva, Clarissa O.
Barbosa, Andre G. H.
Fontes, Rosane A.
Pinheiro, Sergio
Lima, Marco Edilson F.
Castro, Rosane N.
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2011, 22 (04) : 756 - 766
[49] 1,4-Asymmetric induction in reactions between [2-(1-alkoxyalkyl)propenyl](tributyl)stannanes and aldehydes promoted by tin(IV) halides
Gruttadauria, M.
Thomas, E. J.
Acta Chemica Scandinavica, 1994, 4896
[50] Titanium-Mediated Synthesis of 1,4-Diketones from Grignard Reagents and Acyl Cyanohydrins
Setzer, Paul
Beauseigneur, Alice
Pearson-Long, Morwenna S. M.
Bertus, Philippe
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8691 - 8694

← 1 2 3 4 5 →