Diastereoselective ring-closing metathesis in the synthesis of dihydropyrans

被引：65

作者：

Schmidt, B ^{[1
]}

Wildemann, H ^{[1
]}

机构：

[1] Univ Dortmund, Fachbereich Chem, D-44227 Dortmund, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 18期

关键词：

D O I：

10.1021/jo005534x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An investigation into the factors influencing the diastereochemical outcome of the ring-closing metathesis based synthesis of dihydropyrans is presented in this paper. Divinyl carbinols derived from alpha-hydroxy carboxylic acid esters are elaborated to trienes with two diastereotopic vinyl moieties. Depending on the steric demand of the oxo substituent of the divinyl carbinol moiety (either unprotected OH, TBDMS, or benzyl ether) different diastereomers are preferrably formed upon ring-closing metathesis. An extension to diastereoselective double ring-closing metathesis in the formation of spirocycles has also been investigated.

引用

页码：5817 / 5822

页数：6

共 38 条

[1] Zr-catalyzed kinetic resolution of aliphatic cyclic allylic ethers. Carbocycles to heterocycles by Ru- and Mo-catalyzed ring-opening and ring-closing metathesis [J].

Adams, JA ;

Ford, JG ;

Stamatos, PJ ;

Hoveyda, AH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) :9690-9696

[2] Catalytic enantioselective ring-closing metathesis by a chiral biphen-Mo complex [J].

Alexander, JB ;

La, DS ;

Cefalo, DR ;

Hoveyda, AH ;

Schrock, RR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4041-4042

[3]

Armstrong SK, 1998, J CHEM SOC PERK T 1, P371

[4]

AURICH HG, 1991, CHEM BER, V124, P2329

[5]

Clark JS, 1999, TETRAHEDRON, V55, P8231

[6]

Clark JS, 2000, ANGEW CHEM INT EDIT, V39, P372, DOI 10.1002/(SICI)1521-3773(20000117)39:2<372::AID-ANIE372>3.0.CO

[7]

2-Y

[8] Ring-closing metathesis in the synthesis of large and medium-sized oxacycles.: Application to the synthesis of polyoxygenated macrocycles [J].

Delgado, M ;

Martín, JD .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4798-4816

[9] POLYETHER IONOPHORES [J].

DUTTON, CJ ;

BANKS, BJ ;

COOPER, CB .

NATURAL PRODUCT REPORTS, 1995, 12 (02) :165-181

[10] Saturated oxygen heterocycles [J].

Elliott, MC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (09) :1291-1318

← 1 2 3 4 →