Surveying approaches to the formation of carbon-carbon bonds between a pyran and an adjacent ring

被引：16

作者：

Frein, JD ^{[1
]}

Rovis, T ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

TETRAHEDRON | 2006年 / 62卷 / 18期

关键词：

stereoretentive process; Lewis acid; oxocarbenium ions; 1,3]rearrangement;

D O I：

10.1016/j.tet.2006.02.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have examined several methods for the stereoselective formation of carbon-carbon bonds between contiguous rings where a stereogenic center is already present. The approaches investigated were a [1,3] oxygen to carbon rearrangement of cyclic vinyl acetals, an intermolecular enolsilane addition into an in situ generated oxocarbenium ion, an intramolecular conjugate addition of tethered alkoxy enones, and epimerization of several alpha-pyranyl cycloalkanones. These routes have been found to be complementary in several cases and have enabled formation of both the trans:anti and cis:anti stereoisomers in good to excellent yields and varying diastereoselectivities. We have proven C2-C2' relative stereochemistry of 1-2 via a chemical correlation. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：4573 / 4583

页数：11

共 61 条

[1]

ABEL S, 1991, SYNLETT, P171

[2]

Amano S, 1997, SYNLETT, P1300

[3] Substituent effects on the SmI2/Pd(0)-promoted carbohydrate ring-contraction of 5-alkynylpyranosides [J].

Aurrecoechea, JM ;

Gil, JH ;

López, B .

TETRAHEDRON, 2003, 59 (36) :7111-7121

[4]

Awakura D, 2000, SYNLETT, P1733

[5] 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

[6]

Bergmann E.D., 1959, ORG REACTIONS, V10, P179

[7] Synthesis of the C1-C21 (C1′-C21′) fragment of the dimeric polyketide natural product SCH 351448 [J].

Bhattacharjee, A ;

Soltani, O ;

De Brabander, JK .

ORGANIC LETTERS, 2002, 4 (04) :481-484

[8] Pectenotoxin-2 synthetic studies. 2. Construction and conjoining of ABC and DE eastern hemisphere subtargets [J].

Bondar, D ;

Liu, J ;

Muller, T ;

Paquette, LA .

ORGANIC LETTERS, 2005, 7 (09) :1813-1816

[9] Oxygen to carbon rearrangements of anomerically linked alkenols from tetrahydropyran derivatives:: an investigation of the reaction mechanism via a double isotopic labelling crossover study [J].

Buffet, MF ;

Dixon, DJ ;

Edwards, GL ;

Ley, SV ;

Tate, EW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (12) :1815-1827

[10] A NEW PRACTICAL SYNTHESIS OF SILYL ENOL ETHERS .1. FROM SIMPLE ALDEHYDES AND KETONES [J].

CAZEAU, P ;

DUBOUDIN, F ;

MOULINES, F ;

BABOT, O ;

DUNOGUES, J .

TETRAHEDRON, 1987, 43 (09) :2075-2088

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