STEREOSELECTIVE FORMATION OF SUBSTITUTED TETRAHYDROPYRANS BY REACTION OF ALDEHYDES WITH (ETA-3-ALLYL)MOLYBDENUM COMPLEXES

被引：20
作者：
FALLER, JW
LINEBARRIER, DL
机构：
[1] Department of Chemistry, Yale University, New Haven
来源：
ORGANOMETALLICS | 1990年 / 9卷 / 12期
关键词：
D O I：
10.1021/om00162a033
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Substituted tetrahydropyrans are formed in high yield by condensation of 2 mol of aldehyde with molybdenum π-allyls. A [CpMo(NO)(η3-allylXsolvent)]+-BF4- complex is a versatile reagent that provides a convenient route to certain tetrahydropyrans. This moderately stable η3-allyl reagent is conveniently generated by silver-induced halide removal from CpMo(NO)(X)(η3-allyl) complexes. The formation of single isomers of 4-fluoro 2,6-disubstituted tetrahydropyrans is a mild reaction, requiring 6-12 h for completion at room temperature. Spectroscopic evidence suggests intermediate formation of a [CpMo(NO)(allyl)(η1-RCHO)]+BF4- complex. © 1990, American Chemical Society. All rights reserved.
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页码：3182 / 3184
页数：3
相关论文
共 19 条
[1]   alpha-methylenic reactivity in Olefinic systems Part I The prins reaction with propylene [J].
Baker, JW .
JOURNAL OF THE CHEMICAL SOCIETY, 1944, :296-301
[2]  
CHAN TH, 1987, TETRAHEDRON LETT, V28, P3441
[3]   ENANTIOSELECTIVE SYNTHESES OF SECONDARY HOMOALLYL ALCOHOLS WITH OPTICALLY-ACTIVE ETA-3-ALLYLMOLYBDENUM COMPLEXES [J].
FALLER, JW ;
LINEBARRIER, DL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1937-1939
[4]   CONTROLLING STEREOCHEMISTRY IN CROTYL ADDITIONS TO ALDEHYDES WITH CROTYLMOLYBDENUM COMPLEXES [J].
FALLER, JW ;
JOHN, JA ;
MAZZIERI, MR .
TETRAHEDRON LETTERS, 1989, 30 (14) :1769-1772
[5]   CHIRALITY CHANGES IN REACTIONS OF ASYMMETRIC MOLYBDENUM COMPLEXES [J].
FALLER, JW ;
SHVO, Y ;
CHAO, K ;
MURRAY, HH .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1982, 226 (03) :251-275
[6]  
GLADYSZ JA, 1986, ORGANOMETALLICS, V5, P956
[7]   ZUR KENNTNIS DER PRINSSCHEN REAKTION .2. UBER DIE UMSETZUNG VON BUTYLEN MIT FORMALDEHYD [J].
HANSCHKE, E .
CHEMISCHE BERICHTE-RECUEIL, 1955, 88 (07) :1048-1053
[8]  
HESLINGA L, 1966, TRAV CHIM PAYS BAS, V85, P293
[9]  
LEBEL NA, 1963, J ORG CHEM, V28, P615, DOI DOI 10.1021/JO01038A003
[10]  
Mooney E.F., 1968, ANNU REP NMR SPECTRO, V1, P243
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