An improved chiral auxiliary for the allene ether version of the Nazarov cyclization

被引：25

作者：

delos Santos, Derrick B.

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

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 12期

关键词：

D O I：

10.1021/ol060816q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-2-Deoxy-D-glucose derived ether 14 is a superior reagent for the allene ether version of the Nazarov cyclization. Enantiomeric excesses of products derived from trisubstituted morpholino enamides varied between 85% and 93% ee.

引用

页码：2579 / 2582

页数：4

共 20 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] Unique strategy for the assembly of the carbon skeleton of guanacastepene a using an allenic Pauson-Khand-type reaction [J].

Brummond, KM ;

Gao, D .

ORGANIC LETTERS, 2003, 5 (19) :3491-3494

[3] The Nazarov cyclization in organic synthesis. Recent advances [J].

Frontier, AJ ;

Collison, C .

TETRAHEDRON, 2005, 61 (32) :7577-7606

[4]

Habermas K.L., 1994, ORG REACTIONS, V45, P1

[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]

Hausherr A, 2001, SYNTHESIS-STUTTGART, P1377

[10] Study of metal and acid catalysed deprotection of propargyl ethers of alcohols via their allenyl ethers [J].

Mereyala, HB ;

Gurrala, SR ;

Mohan, SK .

TETRAHEDRON, 1999, 55 (37) :11331-11342

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