Influence of β-Substituents in Aldol Reactions of Boron Enolates of β-Alkoxy Methylketones

被引：12

作者：

Dias, Luiz C. ^{[1
]}

de Lucca, Emilio C., Jr. ^{[1
]}

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

Garcia, Danilo C. ^{[1
]}

Tormena, Claudio F. ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

基金：

巴西圣保罗研究基金会;

关键词：

OXYGENATED METHYL KETONES; 1,5-ASYMMETRIC INDUCTION; ADDITION-REACTIONS; 1,5-ANTI STEREOINDUCTION; SILVER TRIFLATE; APRATOXIN-A; FRAGMENT; ALDEHYDES; REMOTE; (+)-ROXATICIN;

D O I：

10.1021/ol102303p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Moderate to good levels of substrate-based 1,5-syn-stereocontrol could be achieved in the boron-mediated aldol reactions of beta-tert-butyl methylketones with achiral aldehydes, independent of the nature of the beta-alkoxy protecting group (P = PMB or TBS). The analysis of the relative energies of the transition structures by theoretical calculations using the density functional B3LYP shows relative energies favoring the corresponding OUT-1,5-SYN transition structures, explaining the observed 1,5-syn stereoinduction.

引用

页码：5056 / 5059

页数：4

共 50 条

[31] Aggregation and Cooperative Effects in the Aldol Reactions of Lithium Enolates
Larranaga, Olatz
de Cozar, Abel
Bickelhaupt, F. Matthias
Zangi, Ronen
Cossio, Fernando P.
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (41) : 13761 - 13773
[32] Computational investigations of aldol reactions of aromatic enolates and aldehydes
Zolfaghari, Arghavan
Wachter, Nanette
Mazumder, Shivnath
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
[33] Evans Enolates: Structures and Mechanisms Underlying the Aldol Addition of Oxazolidinone-Derived Boron Enolates
Zhang, Zirong
Collum, David B.
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (14): : 7595 - 7601
[34] ENANTIOSELECTIVE ALDOL CONDENSATIONS - THE USE OF KETONE BORON ENOLATES WITH CHIRAL LIGANDS ATTACHED TO BORON
PATERSON, I
LISTER, MA
MCCLURE, CK
TETRAHEDRON LETTERS, 1986, 27 (39) : 4787 - 4790
[35] CONCERNING THE DIASTEREOFACIAL SELECTIVITY OF THE ALDOL REACTIONS OF ALPHA-METHYL CHIRAL ALDEHYDES AND LITHIUM AND BORON PROPIONATE ENOLATES
ROUSH, WR
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13): : 4151 - 4157
[36] ASYMMETRIC ALDOL-TYPE REACTIONS OF ACETATE IMIDE ENOLATES
YAN, TH
HUNG, AW
LEE, HC
CHANG, CS
LIU, WH
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3301 - 3306
[37] STEREOSELECTIVE ALDOL CONDENSATION-REACTIONS OF IRON ACETYL ENOLATES
LIEBESKIND, LS
WELKER, ME
TETRAHEDRON LETTERS, 1984, 25 (39) : 4341 - 4344
[38] Catalytic intermolecular aldol reactions of transient amide enolates in domino Michael/aldol reactions of nitroalkanes, acrylamides, and aldehydes
Morita, Shunya
Yoshimura, Tomoyuki
Matsuo, Jun-ichi
GREEN CHEMISTRY, 2021, 23 (03) : 1160 - 1164
[39] STEREOSELECTIVE ALDOL REACTIONS WITH ALPHA-UNSUBSTITUTED CHIRAL ENOLATES
BRAUN, M
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01): : 24 - 37
[40] RECENT ADVANCES IN STEREOSELECTIVE ALDOL REACTIONS OF ESTER AND THIOESTER ENOLATES
BRAUN, M
SACHA, H
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1993, 335 (08): : 653 - 668

← 1 2 3 4 5 →