Catalytic asymmetric oxonium ylide-[2,3] sigmatropic rearrangement with diazocarbonyl compounds: First use of C-2-symmetry in Rh(II) carboxylates.

被引：58

作者：

Pierson, N ^{[1
]}

FernandezGarcia, C ^{[1
]}

McKervey, MA ^{[1
]}

机构：

[1] QUEENS UNIV BELFAST,SCH CHEM,BELFAST BT9 5AG,ANTRIM,NORTH IRELAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(97)01003-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several new chiral rhodium(II) catalysts have been synthesised for evaluation as catalysts in asymmetric oxonium ylide-[2,3] sigmatropic rearrangement of diazocarbonyl substrates; a catalyst derived from (S)-tert-leucine afforded a chiral benzofuranone derivative with an ee of 60 %. (C) 1997 Elsevier Science Ltd.

引用

页码：4705 / 4708

页数：4

共 18 条

[1] ASYMMETRIC-SYNTHESIS OF 1,4-CYCLOHEPTADIENES AND BICYCLO[3.2.1]OCTA-2,6-DIENES BY RHODIUM(II) N-(P-(TERT-BUTYL)PHENYLSULFONYL)PROLINATE CATALYZED-REACTIONS BETWEEN VINYLDIAZOMETHANES AND DIENES
DAVIES, HML
PENG, ZQ
HOUSER, JH
[J]. TETRAHEDRON LETTERS, 1994, 35 (48) : 8939 - 8942
[2] ENANTIOSELECTIVE SYNTHESIS OF VINYLCYCLOPROPANES BY RHODIUM(II) CATALYZED DECOMPOSITION OF VINYLDIAZOMETHANES IN THE PRESENCE OF ALKENES
DAVIES, HML
HUTCHESON, DK
[J]. TETRAHEDRON LETTERS, 1993, 34 (45) : 7243 - 7246
[3] CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS
DOYLE, MP
[J]. CHEMICAL REVIEWS, 1986, 86 (05) : 919 - 939
[4] Chiral catalysts for enantioselective intermolecular cyclopropanation reactions with methyl phenyldiazoacetate. Origin of the solvent effect in reactions catalyzed by homochiral dirhodium(II) prolinates
Doyle, MP
Zhou, QL
Charnsangavej, C
Longoria, MA
McKervey, MA
Garcia, CF
[J]. TETRAHEDRON LETTERS, 1996, 37 (24) : 4129 - 4132
[5] CATALYTIC ASYMMETRIC EPOXIDATION OF UNFUNCTIONALIZED ALKENES USING THE 1ST D4-SYMMETRICAL METALLOTETRAPHENYLPORPHYRIN
HALTERMAN, RL
JAN, ST
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) : 5253 - 5254
[6] JACOBS TL, 1950, J AM CHEM SOC, V72, P256, DOI 10.1021/ja01157a070
[7] A SIMPLE SYNTHESIS OF (S,S)-2,5-HEXANEDIOL
LIESER, JK
[J]. SYNTHETIC COMMUNICATIONS, 1983, 13 (09) : 765 - 767
[8] MCCARTHY N, 1992, TETRAHEDRON LETT, V33, P5883
[9] YLIDE FORMATION FROM THE REACTION OF CARBENES AND CARBENOIDS WITH HETEROATOM LONE PAIRS
PADWA, A
HORNBUCKLE, SF
[J]. CHEMICAL REVIEWS, 1991, 91 (03) : 263 - 309
[10] TOTAL SYNTHESIS OF (+)-GRISEOFULVIN
PIRRUNG, MC
BROWN, WL
REGE, S
LAUGHTON, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) : 8561 - 8562

← 1 2 →