REACTIONS BETWEEN TANTALUM ALKYNE OR NIOBIUM ALKYNE COMPLEXES AND CARBONYL-COMPOUNDS

被引：67

作者：

KATAOKA, Y ^{[1
]}

MIYAI, J ^{[1
]}

OSHIMA, K ^{[1
]}

TAKAI, K ^{[1
]}

UTIMOTO, K ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT IND CHEM,YOSHIDA,KYOTO 60601,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 07期

关键词：

D O I：

10.1021/jo00033a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of tantalum-alkyne complexes are generated in situ by treatment of alkynes with low-valent tantalum derived from TaCl5 and zinc. These complexes add regioselectively to carbonyl compounds in a one-to-one fashion to yield (E)-allylic alcohols stereoselectively. Iodinolysis of the oxatantalacyclopentene, which is postulated as an intermediate of the reaction, gives a (Z)-3-iodo-2-propen-1-ol derivation. In contrast to tantalum-alkyne complexes, niobium-alkyne complexes, prepared with low-valent niobium derived from NbCl5 and zinc, add in situ to aldehydes in a one-to-two fashion to give 1,3-diene derivatives. The dienes are produced through (i) addition of the alkyne complexes with 2 equiv of aldehydes at cis vicinal positions of the alkenes and (ii) deoxygenative elimination of 2,7-dioxanioba-4-cycloheptene complexes.

引用

页码：1973 / 1981

页数：9

共 63 条

[41] SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF A MEERWEIN PONNDORF VERLEY OPPENAUER REDOX INTERMEDIATE AT A TANTALUM(V) CENTER
STRICKLER, JR
BRUCK, MA
WEXLER, PA
WIGLEY, DE
[J]. ORGANOMETALLICS, 1990, 9 (01) : 266 - 273
[42] REACTIVE ALKYNE COMPLEXES OF TANTALUM AND THEIR METALLACYCLIZATION CHEMISTRY - MODELS FOR ALKYNE CYCLOTRIMERIZATION BY THE EARLY TRANSITION-METALS
STRICKLER, JR
WEXLER, PA
WIGLEY, DE
[J]. ORGANOMETALLICS, 1988, 7 (09) : 2067 - 2069
[43] INTERMOLECULAR TAUTOMERIZATION OF METALLACYCLIC IMINES TO ENAMINES FORMED FROM TANTALUM ALKYNE COMPLEXES AND NITRILES
STRICKLER, JR
WIGLEY, DE
[J]. ORGANOMETALLICS, 1990, 9 (05) : 1665 - 1669
[44] METAL-PROMOTED CYCLIZATION .14. ZIRCONACYCLOPROPANES AND ZIRCONACYCLOPROPENES - THEIR SYNTHESIS, CHARACTERIZATION, AND REACTIONS
TAKAHASHI, T
SWANSON, DR
NEGISHI, E
[J]. CHEMISTRY LETTERS, 1987, (04) : 623 - 626
[45] TANTALUM ALKYNE COMPLEXES AS SYNTHETIC INTERMEDIATES - STEREOSELECTIVE PREPARATION OF TRISUBSTITUTED ALLYLIC ALCOHOLS FROM ACETYLENES AND ALDEHYDES
TAKAI, K
KATAOKA, Y
UTIMOTO, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1707 - 1708
[46] REGIOSELECTIVE SYNTHESIS OF HIGHLY SUBSTITUTED FURANS VIA TANTALUM ALKYNE COMPLEXES
TAKAI, K
TEZUKA, M
KATAOKA, Y
UTIMOTO, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (19) : 5310 - 5312
[47] REGIOSELECTIVE AND STEREOSELECTIVE ADDITION OF TANTALUM-1-(ALKYLTHIO)-1-ALKYNE COMPLEXES WITH CARBONYL-COMPOUNDS
TAKAI, K
MIYAI, J
KATAOKA, Y
UTIMOTO, K
[J]. ORGANOMETALLICS, 1990, 9 (12) : 3030 - 3031
[48] REACTION OF TANTALUM-ALKYNE COMPLEXES WITH ISOCYANATES LEADING TO (E)-ALPHA,BETA-UNSATURATED AMIDES - STEREOSELECTIVE FUNCTIONALIZATION OF CARBON-CARBON TRIPLE BONDS
TAKAI, K
KATAOKA, Y
YOSHIZUMI, K
OGUCHI, Y
UTIMOTO, K
[J]. CHEMISTRY LETTERS, 1991, (08) : 1479 - 1482
[49] REACTIONS OF ALKENYLCHROMIUM REAGENTS PREPARED FROM ALKENYL TRIFLUOROMETHANESULFONATES (TRIFLATES) WITH CHROMIUM(II) CHLORIDE UNDER NICKEL CATALYSIS
TAKAI, K
TAGASHIRA, M
KURODA, T
OSHIMA, K
UTIMOTO, K
NOZAKI, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (19) : 6048 - 6050
[50] STEREOSELECTIVE SYNTHESIS OF TRISUBSTITUTED ALPHA,BETA-UNSATURATED ESTERS AND AMIDES VIA REACTIONS OF TANTALUM ALKYNE COMPLEXES DERIVED FROM ACETYLENIC ESTERS AND AMIDES WITH CARBONYL-COMPOUNDS
TAKAI, K
TEZUKA, M
UTIMOTO, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) : 5980 - 5982

← 1 2 3 4 5 6 7 →