On the reactivity of o-lithloaryl ethers:: Tandem anion translocation and Wittig rearrangement

被引:48
作者
Barluenga, J
Fañanás, FJ
Sanz, R
Marcos, C
Trabada, M
机构
[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Mol, Unidad Asociada, CSIC, Oviedo 33071, Spain
[2] Univ Burgos, Fac Ciencias, Dept Quim, Area Quim Organ, Burgos 09001, Spain
关键词
D O I
10.1021/ol0258029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Allyl and benzyl 2-lithloaryl ethers, generated by bromine-lithium exchange in THF, undergo a new tandem anion translocation-[1,2]-Wittig rearrangement allowing the isolation of the corresponding benzylic alcohols.
引用
收藏
页码:1587 / 1590
页数:4
相关论文
共 28 条
[11]   A NOVEL ENTRY INTO WITTIG REARRANGEMENTS - A STEREOSELECTIVE [1,2]-WITTIG REARRANGEMENT WITH INVERSION OF CONFIGURATION AT THE CARBANION CENTER [J].
HOFFMANN, R ;
BRUCKNER, R .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (08) :1957-1963
[12]   Synthesis of optically active aldol derivatives through chirality transfer type 1,2-Wittig rearrangement of α-alkoxycarboxamides [J].
Kitagawa, O ;
Momose, S ;
Yamada, Y ;
Shiro, M ;
Taguchi, T .
TETRAHEDRON LETTERS, 2001, 42 (29) :4865-4868
[13]   Stereospecificity of the 1,2-Wittig rearrangement: How chelation effects influence stereochemical outcome [J].
Maleczka, RE ;
Geng, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8551-8552
[14]  
Marshall J. A., 1991, COMPREHENSIVE ORGANI, V3, P975
[15]   Base-induced cyclization of 1-benzyloxy-2,2,4,4-tetramethylpentan-3-ones: intramolecular nucleophilic addition of an anion of a benzyl ether to the carbonyl moiety without the Wittig rearrangement or protophilic decomposition [J].
Matsumoto, M ;
Watanabe, N ;
Ishikawa, A ;
Murakami, H .
CHEMICAL COMMUNICATIONS, 1997, (24) :2395-2396
[16]   BR-LI-EXCHANGE IN VINYL BROMIDES WITH 2 MOLE-QUIVALENTS OF TERT-BUTYLLITHIUM - REACTIONS OF VINYLLITHIUM COMPOUNDS WITH HETERO AND CARBON ELECTROPHILES [J].
NEUMANN, H ;
SEEBACH, D .
CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (08) :2785-2812
[17]   RECENT RESULTS IN CARBANION CHEMISTRY [J].
SCHOLLKOPF, U .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (10) :763-+
[18]  
SHAFER H, 1968, TETRAHEDRON LETT, P2809
[19]   ALLYLOXY CARBANIONS - NEW SYNTHESIS OF ALDEHYDES VIA A BETA-ACYL CARBANION EQUIVALENT [J].
STILL, WC ;
MACDONAL.TL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (17) :5561-5563
[20]  
Tomooka K, 2000, ANGEW CHEM INT EDIT, V39, P4502, DOI 10.1002/1521-3773(20001215)39:24<4502::AID-ANIE4502>3.0.CO