Iron(III)-catalyzed Prins-type cyclization using homopropargylic alcohol:: A method for the synthesis of 2-alkyl-4-halo-5,6-dihydro-2H-pyrans

被引：114

作者：

Miranda, PO

Díaz, DD

Padrón, JI

Bermejo, J

Martín, VS

机构：

[1] Univ La Laguna, Inst Univ Bioorgan Antonio Gonzalez, San Cristobal la Laguna 38206, Tenerife, Spain

[2] CSIC, Inst Prod Nat & Agrobiol, San Cristobal la Laguna 38206, Tenerife, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 11期

关键词：

D O I：

10.1021/ol034568z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] A new Prins-type cyclization between homopropargylic alcohol and aldehydes in the presence of FeX3 to obtain 2-alkyl-4-halo-5,6-dihydro-2H-pyrans in good yield is described. Osmium-catalyzed cis dihydroxylation provided direct access to trans-2-alkyl-3-hydroxy-tetrahydro-pyran-4-ones. Anhydrous ferric halides are also shown to be excellent catalysts for the standard Prins cyclization using homoallylic alcohol. Isolation of an intermediate acetal provides substantiation of a proposed mechanism.

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页码：1979 / 1982

页数：4

相关论文

共 29 条

[1]

ADAMS DR, 1977, SYNTHESIS-STUTTGART, P661

[2] THE OLEFIN ALDEHYDE CONDENSATION - THE PRINS REACTION [J].

ARUNDALE, E ;

MIKESKA, LA .

CHEMICAL REVIEWS, 1952, 51 (03) :505-555

[3] Stereoselective synthesis of cyclic ethers by intramolecular trapping of dicobalt hexacarbonyl-stabilized propargylic cations [J].

Betancort, JM ;

Martín, T ;

Palazón, JM ;

Martín, VS .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (08) :3216-3224

[4] Stereocontrolled synthesis of cyclic ethers by intramolecular hetero-Michael addition .5. Synthesis of all diastereoisomers of 2,3,5,6-tetrasubstituted tetrahydropyrans [J].

Betancort, JM ;

Martin, VS ;

Padron, JM ;

Palazon, JM ;

Ramirez, MA ;

Soler, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4570-4583

[5] SYNTHETIC ROUTES TO TETRAHYDROFURAN, TETRAHYDROPYRAN, AND SPIROKETAL UNITS OF POLYETHER ANTIBIOTICS AND A SURVEY OF SPIROKETALS OF OTHER NATURAL-PRODUCTS [J].

BOIVIN, TLB .

TETRAHEDRON, 1987, 43 (15) :3309-3362

[6] THE SYNTHESIS OF 4-HALOTETRAHYDROPYRANS AND 4-HALO-5,6-DIHYDRO-2H-PYRANS VIA THE LEWIS ACID PROMOTED CYCLIZATION OF ACETALS OF HOMOALLYLIC AND HOMOPROPARGYLIC ALCOHOLS [J].

BUNNELLE, WH ;

SEAMON, DW ;

MOHLER, DL ;

BALL, TF ;

THOMPSON, DW .

TETRAHEDRON LETTERS, 1984, 25 (25) :2653-2654

[7] Azepines from the intramolecular Prins cyclization of an aminoderivative of lapachol [J].

Camara, CA ;

Pinto, AC ;

Vargas, MD ;

Zukerman-Schpector, J .

TETRAHEDRON, 2002, 58 (30) :6135-6140

[8] ELECTROPHILIC CONDENSATION OF SILYL ETHERS OF HOMOPROPARGYL ALCOHOLS WITH ALDEHYDES - REGIOSELECTIVE SYNTHESIS OF DIHYDROPYRANS [J].

CHAN, TH ;

ARYA, P .

TETRAHEDRON LETTERS, 1989, 30 (31) :4065-4068

[9] Indium trichloride mediated intramolecular Prins-type cyclization [J].

Cho, YS ;

Kim, HY ;

Cha, JH ;

Pae, AN ;

Koh, HY ;

Choi, JH ;

Chang, MH .

ORGANIC LETTERS, 2002, 4 (12) :2025-2028

[10] Stereocontrolled synthesis of trisubstituted tetrahydropyrans [J].

Cloninger, MJ ;

Overman, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (05) :1092-1093