Enantioselective synthesis of sabina ketone

被引：18

作者：

Barberis, M ^{[1
]}

Pérez-Prieto, J ^{[1
]}

机构：

[1] Univ Valencia, ICMOL, Dept Quim Organ, E-46100 Valencia, Spain

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 35期

关键词：

sabina ketone; dirhodium(II) compounds; asymmetric synthesis;

D O I：

10.1016/S0040-4039(03)01629-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both enantiomers of sabina ketone were efficiently prepared via an easy synthesis of 1-diazo-5-methylene-6-methylheptan-2-one, starting from succinic anhydride, followed by its highly enantioselective cyclization catalyzed by chiral dirhodium(II) compounds having ortho-metalated phosphines as ligands. (C) 2003 Published by Elsevier Ltd.

引用

页码：6683 / 6685

页数：3

共 12 条

[1] NEW TOTAL SYNTHESIS OF SABINIC (DL) KETONE [J].

ALEXANDRE, C ;

ROUESSAC, F .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (07) :2241-+

[2] Chiral dirhodium(II) catalysts with ortho-metalated arylphosphine ligands:: Synthesis and application to the enantioselective cyclopropanation of α-diazo ketones [J].

Barberis, M ;

Pérez-Prieto, J ;

Herbst, K ;

Lahuerta, P .

ORGANOMETALLICS, 2002, 21 (08) :1667-1673

[3]

BOER TJD, 1963, ORG SYNTH, V4, P250

[4] SABINENE HYDRATE - A CONSTITUENT OF AMERICAN PEPPERMINT OIL [J].

DALY, JW ;

GREEN, FC ;

EASTMAN, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (23) :6330-6336

[5] TOTAL SYNTHESIS OF DL-SABINENE DL-TRANS-SABINENE HYDRATE AND RELATED MONOTERPENES [J].

FANTA, WI ;

ERMAN, WF .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (04) :1656-&

[6] A short and efficient synthesis of (±)-trans-sabinene hydrate [J].

Galopin, CC .

TETRAHEDRON LETTERS, 2001, 42 (33) :5589-5591

[7] BASE INDUCED ISOMERIZATIONS OF GAMMA,DELTA-EPOXYKETONES .2. SYNTHESES IN THUJANE SERIES - D,L-SABINA KETONE AND D,L-CIS-SABINENE HYDRATE [J].

GAONI, Y .

TETRAHEDRON, 1972, 28 (22) :5525-&

[8] Ozonides of mono-, bi- and tricyclic terpenes [J].

Griesbaum, K ;

Hilss, M ;

Bosch, J .

TETRAHEDRON, 1996, 52 (47) :14813-14826

[9] A CONVENIENT SYNTHESIS OF 5-ALKYLBICYCLO[3.1.0]HEXAN-2-ONES INCLUDING THE NATURAL PRODUCT SABINA KETONE [J].

HAMON, DPG ;

SHIRLEY, NJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (07) :1321-1325

[10] HOMOCHIRAL KETALS IN ORGANIC-SYNTHESIS - DIASTEREOSELECTIVE CYCLOPROPANATION OF ALPHA,BETA-UNSATURATED KETALS DERIVED FROM 1,4-DI-O-BENZYL-L-THREITOL [J].

MASH, EA ;

NELSON, KA .

TETRAHEDRON, 1987, 43 (04) :679-692

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