p-Menthane-3-carboxaldehyde:: A useful chiral auxiliary for the synthesis of chiral quaternary carbons of high enantiomeric purity

被引：44

作者：

Spino, C ^{[1
]}

Godbout, C ^{[1
]}

Beaulieu, C ^{[1
]}

Harter, M ^{[1
]}

Mwene-Mbeja, TM ^{[1
]}

Boisvert, L ^{[1
]}

机构：

[1] Univ Sherbrooke, Dept Chim, Sherbrooke, PQ J1K 2R1, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 41期

关键词：

D O I：

10.1021/ja046084j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(+)- or (-)-p-Menthane-3-carboxaldehyde is made in two easy steps from (+)- or (-)-menthone, respectively. This auxiliary allows for the synthesis of carbonyl compounds bearing a a-chiral quaternary carbon. The flexibility, efficiency, and ease of use of the method are demonstrated in a series of examples, which include the total synthesis of (+)-cuparenone as well as a partial synthesis of (-)-cassiol.

引用

页码：13312 / 13319

页数：8

共 45 条

[1] GENERAL METHOD FOR SYNTHESIS OF HIGH ENANTIOMERIC PURITY CHIRAL EPOXIDES
PIRKLE, WH
RINALDI, PL
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (20): : 3803 - 3807
[2] Unprecedented base effect on the synthesis of chiral phosphinate esters: A new route to P-chiral phosphine oxides of high enantiomeric purity
Benabra, A
Alcudia, A
Khiar, N
Fernandez, I
Alcudia, F
TETRAHEDRON-ASYMMETRY, 1996, 7 (12) : 3353 - 3356
[3] A novel method to generate chiral quaternary carbon centers of high enantiomeric purity using a highly stereoselective addition of vinylalanes to a chiral aldehyde
Spino, C
Beaulieu, C
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (11) : 1930 - +
[4] A NOVEL DISPLACEMENT ROUTE TO P-CHIRAL PHOSPHINE OXIDES OF HIGH ENANTIOMERIC PURITY
CARDELLICCHIO, C
FIANDANESE, V
NASO, F
PACIFICO, S
KOPROWSKI, M
PIETRUSIEWICZ, KM
TETRAHEDRON LETTERS, 1994, 35 (34) : 6343 - 6346
[5] SIMPLE P-31 NMR METHOD FOR THE DETERMINATION OF ENANTIOMERIC PURITY OF ALCOHOLS NOT REQUIRING CHIRAL AUXILIARY COMPOUNDS
FERINGA, BL
SMAARDIJK, A
WYNBERG, H
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (16) : 4798 - 4799
[6] STEREOSELECTIVE CONSTRUCTION OF QUATERNARY CARBON CENTERS VIA REACTION OF HETEROCUPRATES WITH CHIRAL ALLENIC BROMIDES - A FACILE SYNTHESIS OF BUTYLETHYLMETHYLPROPYLMETHANE IN HIGH ENANTIOMERIC PURITY
CAPORUSSO, AM
CONSOLONI, C
LARDICCI, L
GAZZETTA CHIMICA ITALIANA, 1988, 118 (12): : 857 - 859
[7] AN ASYMMETRIC-SYNTHESIS OF CHIRAL 4,4-DISUBSTITUTED CYCLOHEXENONES IN HIGH ENANTIOMERIC PURITY
MEYERS, AI
LEFKER, BA
WANNER, KT
AITKEN, RA
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (10): : 1936 - 1938
[8] SYNTHESIS AND ENANTIOMERIC PURITY DETERMINATION OF CHIRAL 3-BENZYLGLYCIDOL, A KEY SYNTHON FOR HIV PROTEASE INHIBITORS
SHUM, WP
CHEN, J
CANNARSA, MJ
CHIRALITY, 1994, 6 (08) : 681 - 684
[9] 3,3-DIMETHYLALLYLDIISOPINOCAMPHEYLBORANE - A NOVEL REAGENT FOR CHIRAL ISOPRENYLATION OF ALDEHYDES - SYNTHESIS OF (+)-ARTEMISIA AND (-)-ARTEMISIA ALCOHOL IN EXCEPTIONALLY HIGH ENANTIOMERIC PURITY
BROWN, HC
JADHAV, PK
TETRAHEDRON LETTERS, 1984, 25 (12) : 1215 - 1218
[10] 1H and 31P NMR determination of the enantiomeric purity of quaternary phosphonium cations using TRISPHAT as chiral shift agent
Ginglinger, C
Jeannerat, D
Lacour, J
Jugé, S
Uziel, J
TETRAHEDRON LETTERS, 1998, 39 (41) : 7495 - 7498

← 1 2 3 4 5 →