Unprecedented alkene stereocontrol in the Claisen rearrangement of cyclic bis-allylic esters

被引：7

作者：

McFarland, C ^{[1
]}

Hutchison, J ^{[1
]}

McIntosh, MC ^{[1
]}

机构：

[1] Univ Arkansas, Dept Chem & Biochem, Fayetteville, AR 72701 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 17期

关键词：

D O I：

10.1021/ol0511732

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The Ireland and ester enolate Claisen rearrangements of tertiary substituted bis-allylic esters derived from cyclohexenones afford pentenoic acids that possess tri- and tetrasubstituted alkylidenes with unprecedented levels of stereoselectivity. In some cases the higher energy exocyclic alkene is the major product.

引用

页码：3641 / 3644

页数：4

共 30 条

[1] REGIOSELECTIVITY IN THE CLAISEN REARRANGEMENT OF BIS-ALLYLIC ALCOHOLS - ELECTRONIC AND STERIC EFFECTS OF C-4 SUBSTITUENTS
PARKER, KA
FARMAR, JG
TETRAHEDRON LETTERS, 1985, 26 (31) : 3655 - 3658
[2] Acyclic stereocontrol in the Ireland-Claisen rearrangement of α-branched esters
Qin, Ying-Chuan
Stivala, Craig. E.
Zakarian, Armen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) : 7466 - 7469
[3] Factors influencing the rearrangement of bis-allylic hydroperoxides by manganese lipoxygenase
Oliw, Ernst H.
JOURNAL OF LIPID RESEARCH, 2008, 49 (02) : 420 - 428
[4] Decarboxylative claisen rearrangement reactions of allylic tosylmalonate esters
Craig, D
Grellepois, F
ORGANIC LETTERS, 2005, 7 (03) : 463 - 465
[5] The ester enolate Claisen ring closing metathesis manifold: An alternative to rearrangement of cyclic allylic esters
Miller, JF
Koch, K
Piscopio, AD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 266 - ORGN
[6] Comparison of ester enolate and silylketene acetal variants of the Ireland Claisen rearrangements in bis-allylic substrates
Nelsen, C
Hong, SP
McIntosh, MC
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U376 - U376
[7] HIGHLY ENANTIOSELECTIVE AND DIASTEREOSELECTIVE IRELAND-CLAISEN REARRANGEMENT OF ACHIRAL ALLYLIC ESTERS
COREY, EJ
LEE, DH
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) : 4026 - 4028
[8] Stereochemical control in the silyl triflate-mediated Claisen rearrangement of allylic esters
Kobayashi, M
Masumoto, K
Nakai, E
Nakai, T
TETRAHEDRON LETTERS, 1996, 37 (17) : 3005 - 3008
[9] ACYCLIC STEREOCONTROL THROUGH THE DIANIONIC CLAISEN REARRANGEMENT OF BETA-HYDROXY ESTERS - SYNTHESIS OF (+/-)-BOTRYODIPLODIN
KURTH, MJ
YU, CM
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11): : 1840 - 1845
[10] Inter- and intramolecular decarboxylation of bis-allylic esters lacking anion-stabilizing groups
Hyatt, Ivan
Croatt, Mitch
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250

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