Short stereoselective route to γ-CF3 allylic alcohols:: Rearrangements with creation of quaternary CF3-substituted carbons

被引：23

作者：

Bouvet, D

Sdassi, H

Ourévitch, M

Bonnet-Delpon, D

机构：

[1] BioCIS, UPRES A8076, Ctr Etud Pharmaceut, F-92296 Chatenay Malabry, France

[2] Univ Chouaib Doukkali, Fac Sci, El Jadida, Morocco

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 07期

关键词：

D O I：

10.1021/jo991702d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise preparation of tetrasubstituted hindered functionalized CF3-olefins 2-7 from corresponding enol ether 3 is described. Geometrically pure gamma-CF3,gamma-alkyl allylic alcohol thus prepared could undergo Claisen-type rearrangements and provide, in good yields, carboxylic esters and amides containing a beta- quaternary CF3-substituted carbon.

引用

页码：2104 / 2107

页数：4

共 24 条

[1] Addition of organolithium reagents to alpha-(trifluoromethyl)styrene: Concise synthesis of functionalised gem-difluoroalkenes
Begue, JP
BonnetDelpon, D
Rock, MH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12): : 1409 - 1413
[2] THE WITTIG REACTION OF PERFLUORO-ACID DERIVATIVES - ACCESS TO FLUORINATED ENOL ETHERS, ENAMINES, AND KETONES
BEGUE, JP
BONNETDELPON, D
MESUREUR, D
NEE, G
WU, SW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3807 - 3814
[3] CLAISEN REARRANGEMENT OF ALPHA-(F-ALKYL)ENOL ETHERS PREPARED VIA WITTIG OLEFINATION OF ALLYL PERFLUOROALKANOATES
BEGUE, JP
BONNETDELPON, D
WU, SW
MBIDA, A
SHINTANI, T
NAKAI, T
[J]. TETRAHEDRON LETTERS, 1994, 35 (18) : 2907 - 2910
[4] Synthesis of hindered and functionalized 1-CF3 substituted olefins via a carbolithiation-elimination-metalation cascade
Begue, JP
BonnetDelpon, D
Bouvet, D
Rock, MH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) : 9111 - 9114
[5] MICHAEL AND ANTI-MICHAEL ADDITIONS TO BENZOYL(TRIFLUOROMETHYL)ACETYLENE
BUMGARDNER, CL
BUNCH, JE
WHANGBO, MH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (21) : 4082 - 4083
[6] INSECT CHEMISTRY .6. TRIFLUOROMETHYL ANALOGS OF JUVENILE HORMONES
CAMPS, F
CANELA, R
COLL, J
MESSEGUER, A
ROCA, A
[J]. TETRAHEDRON, 1978, 34 (14) : 2179 - 2182
[7] ENERGETIC AND RATE EFFECTS OF THE TRIFLUOROMETHYL GROUP AT C-2 AND C-4 ON THE ALIPHATIC CLAISEN REARRANGEMENT
GAJEWSKI, JJ
GEE, KR
JURAYJ, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1813 - 1822
[8] HADDAD M, 1994, SYNTHESIS-STUTTGART, P167
[9] HYDROMETALLATION OF 1-ALKYL-3-TRIFLUOROMETHYL PROPARGYL ALCOHOLS
HANZAWA, Y
KAWAGOE, K
TANAHASHI, N
KOBAYASHI, Y
[J]. TETRAHEDRON LETTERS, 1984, 25 (42) : 4749 - 4752
[10] SYNTHESES OF TRIFLUOROMETHYLATED DIENE DERIVATIVES THROUGH THE CLAISEN REARRANGEMENT OF TRIFLUOROMETHYLATED PROPARGYLIC AND ALLYLIC ALCOHOLS
HANZAWA, Y
KAWAGOE, K
YAMADA, A
KOBAYASHI, Y
[J]. TETRAHEDRON LETTERS, 1985, 26 (02) : 219 - 222

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