2-SUBSTITUTED (E)-2-(2-LITHIOETHENYL)-1,3-DIOXOLANES - NEW DIASTEREOISOMERIC PURE BETA-ACYLVINYL ANION EQUIVALENTS

被引：19

作者：

BACHKI, A ^{[1
]}

FOUBELO, F ^{[1
]}

YUS, M ^{[1
]}

机构：

[1] UNIV ALICANTE, FAC CIENCIAS, DEPT QUIM ORGAN, E-03080 ALACANT, SPAIN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 41期

关键词：

D O I：

10.1016/S0040-4039(00)78364-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of (E)-chloroketals 1 with lithium powder and a catalytic amount of DTBB (4 mol %) in THF at -90 degrees C followed by treatment with different electrophiles [H2O, D2O, Bu(t)CHO, PhCHO, Me(2)CO,(CH2)(4)CO, PhCOMe] at -90 to -60 degrees C affords, after hydrolysis with water, the expected functionalised protected (E)-alpha,beta-unsaturated ketones 3. The deprotection of products 3 is easily achieved with silica gel/aqueous oxalic acid (cat.) to yield (E)-functionalised alkenones 5.

引用

页码：7643 / 7646

页数：4

共 56 条

[1] N,2-DILITHIOALKYLAMINES FROM AZIRIDINES BY NAPHTHALENE-CATALYZED REDUCTIVE OPENING - SYNTHETIC APPLICATIONS
ALMENA, J
FOUBELO, F
YUS, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) : 3210 - 3215
[2] NAPHTHALENE-CATALYZED REDUCTIVE OPENING OF AZIRIDINES WITH LITHIUM - A DIRECT PREPARATION OF N-LITHIO-2-LITHIOALKYLAMINES
ALMENA, J
FOUBELO, F
YUS, M
[J]. TETRAHEDRON LETTERS, 1993, 34 (10) : 1649 - 1652
[3] 4,4'-DI-TERT-BUTYLBIPHENYL-CATALYZED REDUCTIVE OPENING OF AZETIDINES WITH LITHIUM - A DIRECT PREPARATION OF 3,N-DILITHIOALKYLAMINES
ALMENA, J
FOUBELO, F
YUS, M
[J]. TETRAHEDRON, 1994, 50 (19) : 5775 - 5782
[4] GAMMA-SUBSTITUTED BUTYROLACTONES FROM ACROLEIN AND CARBONYL-COMPOUNDS
BARLUENGA, J
FERNANDEZ, JR
YUS, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (20) : 1534 - 1535
[5] BARLUENGA J, 1986, J CHEM RES-S, P218
[6] 3,3-DIETHOXYPROPYL-LITHIUM - A MASKED LITHIUM PROPANAL HOMOENOLATE
BARLUENGA, J
RUBIERA, C
FERNANDEZ, JR
YUS, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (06) : 425 - 426
[7] 3,3-DIETHOXYPROPYL-LITHIUM - A MASKED LITHIUM PROPANAL HOMOENOLATE IN ORGANIC-SYNTHESIS
BARLUENGA, J
FERNANDEZ, JR
RUBIERA, C
YUS, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (12): : 3113 - 3117
[8] BARLUENGA J, 1986, J CHEM RES-S, P2401
[9] HOMOENOLATES AND OTHER FUNCTIONALIZED ORGANOMETALLICS - A REVIEW
CRIMMINS, MT
NANTERMET, PG
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1993, 25 (01) : 41 - 81
[10] NEW MASKED DELTA-LITHIOCARBONYL COMPOUNDS - PREPARATION AND SYNTHETIC APPLICATIONS
GIL, JF
RAMON, DJ
YUS, M
[J]. TETRAHEDRON, 1993, 49 (22) : 4923 - 4938

← 1 2 3 4 5 6 →