TBAF-Mediated Aldol Reaction of β-Allenoates: Regio- and Stereoselective Synthesis of (2E,4E)-4-Carbinol Alkadienoates

被引:19
作者
Aponte, Jose C. [1 ]
Hammond, Gerald B. [1 ]
Xu, Bo [1 ]
机构
[1] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
基金
美国国家科学基金会;
关键词
VINYLOGOUS MANNICH REACTION; CHIRAL AMBIDENT NUCLEOPHILES; EFFICIENT SYNTHESIS; CATALYZED SYNTHESIS; ALKYNYL ESTERS; ALLENYL ESTERS; ACID; FRAGMENT; 2-HYDROXY-3,4-DIENOATES; REARRANGEMENT;
D O I
10.1021/jo900567m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aldol reaction of beta-allenoate with use of a commercial THF solution of tetrabutylammonium fluoride (TBAF) yielded polyfunctionalized (2E,4E)-4-carbinol alkadienoate-a valuable building block-in highly regio- and stereoselective fashion.
引用
收藏
页码:4623 / 4625
页数:3
相关论文
共 52 条
[1]   REACTION OF COPPER ENOLATES OF ESTERS WITH PROPARGYLIC SYSTEMS - FACILE PREPARATION OF 3,4-DIENOIC ESTERS, STEREOSELECTIVE REARRANGEMENT TO (2E,4Z)-DIENOIC AND (2E,4E)-DIENOIC ESTERS, AND STEREOSELECTIVE SYNTHESIS OF A FRAGRANCE FROM BARTLETT PEAR [J].
AMOS, RA ;
KATZENELLENBOGEN, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (04) :555-560
[2]   Formal syntheses of (+/-)-pinnaic acid and (+/-)-halichlorine [J].
Andrade, RB ;
Martin, SF .
ORGANIC LETTERS, 2005, 7 (25) :5733-5735
[3]   ALLENYL ENOLATES - A NEW CLASS OF CHIRAL AMBIDENT NUCLEOPHILES .1. REACTION WITH C-ELECTROPHILES AND SI-ELECTROPHILES [J].
ARNDT, S ;
HANDKE, G ;
KRAUSE, N .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (01) :251-259
[4]   A highly efficient and practical method for catalytic asymmetric vinylogous Mannich (AVM) reactions [J].
Carswell, Emma L. ;
Snapper, Marc L. ;
Hoveyda, Amir H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (43) :7230-7233
[5]   The vinylogous aldol reaction: A valuable, yet understated carbon-carbon bond-forming maneuver [J].
Casiraghi, G ;
Zanardi, F ;
Appendino, G ;
Rassu, G .
CHEMICAL REVIEWS, 2000, 100 (06) :1929-1972
[6]   Palladium-catalyzed synthesis of 1,3-dienes from allenes and organic halides [J].
Chang, HM ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) :1767-1773
[7]   Rhodium-catalyzed synthesis of eight-membered rings [J].
DeBoef, Brenton ;
Counts, W. Richard ;
Gilbertson, Scott R. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (03) :799-804
[8]  
Denmark SE, 2005, ANGEW CHEM INT EDIT, V44, P4682, DOI 10.1002/anie.200462338
[9]  
Enders D, 2000, CHEM-EUR J, V6, P1302
[10]   Ambiphilic allenyl enolates [J].
Fredrick, MA ;
Hulce, M .
TETRAHEDRON, 1997, 53 (30) :10197-10227