alpha-Allylation of carbonyl compounds via silyl enol ethers and silyl ketene acetals using a hypervalent iodine reagent

被引：4

作者：

Moriarty, RM

Epa, WR

Prakash, O

机构：

[1] Chemistry Department, University of Illinois at Chicago, Chicago, IL 60607

来源：

JOURNAL OF CHEMICAL RESEARCH-S | 1997年 / 07期

关键词：

D O I：

10.1039/a701224a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of allyltrimethylsilane with iodosobenzene and trimethylsilyl trifluoromethanesulfonate followed by treatment with trimethylsilyl enol ethers of ketones or trimethylsilyl ketene acetals of esters/lactones provides a new method for the alpha-allylation of the corresponding carbonyl compounds.

引用

页码：262 / 263

页数：3

共 50 条

[31] NEW SYNTHETIC METHODS FOR ALPHA, BETA-UNSATURATED KETONES, ALDEHYDES, ESTERS AND LACTONES BY THE PALLADIUM-CATALYZED REACTIONS OF SILYL ENOL ETHERS, KETENE SILYL ACETALS, AND ENOL ACETATES WITH ALLYL CARBONATES
MINAMI, I
TAKAHASHI, K
SHIMIZU, I
KIMURA, T
TSUJI, J
TETRAHEDRON, 1986, 42 (11) : 2971 - 2977
[32] Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers
Shen, Hang
Li, Jiaqiang
Liu, Qing
Pan, Jing
Huang, Ruofeng
Xiong, Yan
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (14): : 7212 - 7218
[33] Photoaddition reactions of silyl ketene acetals with aromatic carbonyl compounds:: A new procedure for β-hydroxyester synthesis
Yoon, UC
Kim, MJ
Moon, JJ
Oh, SW
Kim, HJ
Mariano, PS
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2002, 23 (09) : 1218 - 1228
[34] CLAY MONTMORILLONITE-CATALYZED ALDOL REACTIONS OF SILYL KETENE ACETALS WITH CARBONYL-COMPOUNDS
ONAKA, M
OHNO, R
KAWAI, M
IZUMI, Y
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (07) : 2689 - 2691
[35] Lewis base catalyzed Michael reaction between ketene silyl acetals and α,β-unsaturated carbonyl compounds
Mukaiyama, T
Nakagawa, T
Fujisawa, H
CHEMISTRY LETTERS, 2003, 32 (01) : 56 - 57
[36] HIGHLY CONVENIENT ELECTROLYSIS PROCEDURE FOR THE PREPARATION OF ALPHA-HALOGENATED KETONES AND ACETALS FROM ENOL ACETATES, ENOL ETHERS, AND SILYL ENOL ETHERS
TORII, S
INOKUCHI, T
MISIMA, S
KOBAYASHI, T
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (13): : 2731 - 2735
[37] SILYL KETONE CHEMISTRY - SYNTHESIS OF REGIOISOMERICALLY AND STEREOISOMERICALLY PURE ENOL SILYL ETHERS USING ALPHA-PHENYLTHIO SILYL KETONES
REICH, HJ
HOLTAN, RC
BORKOWSKY, SL
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (02): : 312 - 314
[38] HYPERVALENT IODINE OXIDATION OF SILYL ENOL ETHERS USING BF3.ETO AND METHANOL - A SIMPLE ROUTE TO ALPHA-METHOXY ARYLMETHYL KETONES
MORIARTY, RM
PRAKASH, O
DUNCAN, MP
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1985, 190 (SEP): : 186 - ORN
[39] REACTION OF SILYL ENOL ETHERS WITH PHOSPHITE USING HYPERVALENT IODINE COMPOUND - A NEW SYNTHESIS OF 2-ARYL-2-OXOALKYLPHOSPHONATES
KIM, DY
MANG, JY
OH, DY
SYNTHETIC COMMUNICATIONS, 1994, 24 (05) : 629 - 634
[40] The Use of Silyl Ketene Acetals and Enol Ethers in the Catalytic Enantioselective Alkylative Ring Opening of Oxa/Aza Bicyclic Alkenes
Zhang, Lei
Le, Christine M.
Lautens, Mark
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) : 5951 - 5954

← 1 2 3 4 5 →