Design of chiral auxiliaries for the allene ether Nazarov cyclization

被引:41
作者
Banaag, April R.
Tius, Marcus A.
机构
[1] Univ Hawaii, Dept Chem, Honolulu, HI 96822 USA
[2] Canc Res Ctr Hawaii, Honolulu, HI 96813 USA
关键词
D O I
10.1021/ja069342g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. alpha-Pyranose and beta-pyranose derived auxiliaries lead to enantiomeric products.
引用
收藏
页码:5328 / +
页数:3
相关论文
共 17 条
[1]   Stereochemistry of nucleophilic substitution reactions depending upon substituent: Evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents [J].
Ayala, L ;
Lucero, CG ;
Romero, JAC ;
Tabacco, SA ;
Woerpel, KA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (50) :15521-15528
[2]   An improved chiral auxiliary for the allene ether version of the Nazarov cyclization [J].
delos Santos, Derrick B. ;
Banaag, April R. ;
Tius, Marcus A. .
ORGANIC LETTERS, 2006, 8 (12) :2579-2582
[3]   The Nazarov cyclization in organic synthesis. Recent advances [J].
Frontier, AJ ;
Collison, C .
TETRAHEDRON, 2005, 61 (32) :7577-7606
[4]   A new approach to the Nazarov reaction via sequential electrocyclic ring opening and ring closure [J].
Grant, Tina N. ;
West, F. G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (29) :9348-9349
[5]  
Harmata M., 2004, CHEMTRACTS, V17, P416
[6]   Asymmetric cyclopentannelation: Camphor-derived auxiliary [J].
Harrington, PE ;
Murai, T ;
Chu, C ;
Tius, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10091-10100
[7]   Asymmetric cyclopentannelation. Chiral auxiliary on the allene [J].
Harrington, PE ;
Tius, MA .
ORGANIC LETTERS, 2000, 2 (16) :2447-2450
[8]   Synthesis and absolute stereochemistry of roseophilin [J].
Harrington, PE ;
Tius, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (35) :8509-8514
[9]   Tandem Nazarov cyclization-Michael addition sequence catalyzed by an Ir(III) complex [J].
Janka, M ;
He, W ;
Haedicke, IE ;
Fronczek, FR ;
Frontier, AJ ;
Eisenberg, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (16) :5312-5313
[10]   Enantioselective Nazarov reactions through catalytic asymmetric proton transfer [J].
Liang, GX ;
Trauner, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9544-9545