ON THE UTILITY OF ALPHA-HETEROATOM SUBSTITUTED ORTHOESTERS IN THE JOHNSON-CLAISEN REARRANGEMENT

被引：7

作者：

ELWORTHY, TR ^{[1
]}

MORGANS, DJ ^{[1
]}

PALMER, WS ^{[1
]}

REPKE, DB ^{[1
]}

SMITH, DB ^{[1
]}

WALTOS, AM ^{[1
]}

机构：

[1] SYNTEX INC,DISCOVERY RES,INST ORGAN CHEM,PALO ALTO,CA 94304

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 28期

关键词：

D O I：

10.1016/S0040-4039(00)73290-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Heteroatom substituted orthoesters were prepared and found to undergo the Johnson Claisen rearrangement with a variety of allylic alcohols giving gamma,delta-unsaturated alpha-heteroatom substituted esters in fair to excellent yields. The diastereoselectivity of the process was examined.

引用

页码：4951 / 4954

页数：4

共 34 条

[1] THE ESTER ENOLATE CLAISEN REARRANGEMENT OF ALLYL ALPHA-HYDROXYACETATES AND ALPHA-PHENYLTHIOACETATES
AGER, DJ
COOKSON, RC
[J]. TETRAHEDRON LETTERS, 1982, 23 (33) : 3419 - 3420
[2] BARTLETT PA, 1980, TETRAHEDRON, V36, P2
[3] BENNETT GB, 1977, SYNTHESIS-STUTTGART, P589
[4] THE HETERO-COPE REARRANGEMENT IN ORGANIC-SYNTHESIS
BLECHERT, S
[J]. SYNTHESIS-STUTTGART, 1989, (02): : 71 - 82
[5] SYNTHETIC STUDIES DIRECTED TOWARD NATURALLY-OCCURRING TETRAMIC ACIDS .3. SYNTHESIS OF (-)-METHYL YDIGINATE AND THE TETRAMIC ACID SUBUNIT FOR STREPTOLYDIGIN
BOECKMAN, RK
POTENZA, JC
ENHOLM, EJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (03) : 469 - 472
[6] ON THE COHERENCE OF INCORPORATION OF THE FLUOROVINYL MOIETY INTO BIOACTIVE ORGANIC-COMPOUNDS - SYNTHESIS OF AN INSECT JUVENILE HORMONE-III FLUORINATED ANALOG
CAMPS, F
MESSEGUER, A
SANCHEZ, FJ
[J]. TETRAHEDRON, 1988, 44 (16) : 5161 - 5167
[7] The rearrangement of phenol-allyl-ather in C-allyl-phenole
Claisen, L
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1912, 45 : 3157 - 3166
[8] THE STEREOCONTROLLED CLAISEN REARRANGEMENT OF TERTIARY ALLYLIC SULFONE ESTERS - STEREOSELECTIVE FORMATION OF TRISUBSTITUTED DOUBLE-BONDS
DAVIDSON, AH
EGGLETON, N
WALLACE, IH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) : 378 - 380
[9] (E)-3-(TRIMETHYLSILYL)-2-PROPEN-1-OL - AN IMPROVED PREPARATION
DENMARK, SE
JONES, TK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (23) : 4595 - 4597
[10] SIMPLE SYNTHESIS OF OPTICALLY-ACTIVE 2-FLUOROPROPANOIC ACID AND ANALOGS OF HIGH ENANTIOMERIC PURITY
FRITZLANGHALS, E
SCHUTZ, G
[J]. TETRAHEDRON LETTERS, 1993, 34 (02) : 293 - 296

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