1,5-asymmetric induction in boron-mediated aldol reactions of β-alkoxy methylketones

被引：22

作者：

Dias, Luiz C. ^{[1
]}

de Marchi, Anderson A. ^{[1
]}

Ferreira, Marco A. B. ^{[1
]}

Aguilar, Andrea M. ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Quim, BR-13084971 Campinas, SP, Brazil

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 16期

关键词：

D O I：

10.1021/jo8009165

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Good levels of substrate-controlled, 1,5-syn-stereoinduction are obtained in boron-mediated aldol reactions of beta-trichloromethyl-beta-alkoxy and beta-trifluoromethyl-beta-alkoxy methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group (TBS or PMB). In the case of boron aldol reactions of beta-aryl-beta-alkoxy methylketones, the 1,5-anti-adducts were obtained with high levels of diastereoselectivity only with a beta-OPMB group.

引用

页码：6299 / 6311

页数：13

共 66 条

[1] [Anonymous], [No title captured]
[2] [Anonymous], 1997, ORG REACT
[3] A NEW METHOD FOR THE PREPARATION OF TERTIARY BUTYL ETHERS AND ESTERS
ARMSTRONG, A
BRACKENRIDGE, I
JACKSON, RFW
KIRK, JM
[J]. TETRAHEDRON LETTERS, 1988, 29 (20) : 2483 - 2486
[4] AN APPROACH TO THE SYNTHESIS OF BACTOBOLIN AND THE TOTAL SYNTHESIS OF N-ACETYLACTINOBOLAMINE - SOME REMARKABLY STABLE HEMIACETALS
ASKIN, D
ANGST, C
DANISHEFSKY, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (04) : 622 - 635
[5] Supramolecular silanol chemistry in the gas phase.: Topological (AIM) and population (NBO) analyses of hydrogen-bonded complexes between H3SiOH and selected O- and N-acceptor molecules
Beckmann, Jens
Grabowsky, Simon
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2007, 111 (10) : 2011 - 2019
[6] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
Begue, Jean-Pierre
Bonnet-Delpon, Daniele
[J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) : 992 - 1012
[7] AN MC-SCF STUDY OF THE TRANSITION STRUCTURES FOR THE ALDOL REACTION OF FORMALDEHYDE WITH ACETALDEHYDE BORON ENOLATE
BERNARDI, F
ROBB, MA
SUZZIVALLI, G
TAGLIAVINI, E
TROMBINI, C
UMANIRONCHI, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) : 6472 - 6475
[8] SYNTHESIS OF BRYOSTATINS .1. CONSTRUCTION OF THE C(1)-C(16) FRAGMENT
BLANCHETTE, MA
MALAMAS, MS
NANTZ, MH
ROBERTS, JC
SOMFAI, P
WHRITENOUR, DC
MASAMUNE, S
KAGEYAMA, M
TAMURA, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) : 2817 - 2825
[9] ARE CHELATES TRULY INTERMEDIATES IN CRAMS CHELATE RULE
CHEN, XN
HORTELANO, ER
ELIEL, EL
FRYE, SV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (16) : 6130 - 6131
[10] Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water
Chimni, SS
Mahajan, D
[J]. TETRAHEDRON, 2005, 61 (21) : 5019 - 5025

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