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

[31] CHIRAL SULFUR-COMPOUNDS .24. A CONVENIENT SYNTHESIS OF 2-METHOXY-1-NAPTHYL SULFOXIDES IN HIGH ENANTIOMERIC PURITY - A NEW ASYMMETRIC-SYNTHESIS OF 1-BENZYL-1,2,3,4-TETRAHYDROISOQUINOLINES
PYNE, SG
HAJIPOUR, AR
PRABAKARAN, K
TETRAHEDRON LETTERS, 1994, 35 (04) : 645 - 648
[32] Catalytic Enantioselective Hydrovinylation of Trialkylsilyloxy and Acetoxy-1,3-Dienes: Cationic Co(I) Complexes for the Synthesis of Chiral Enolate Surrogates and Their Applications for Synthesis of Ketones and Cross-Coupling Reagents in High Enantiomeric Purity
Biswas, Souvagya
Dewese, Kendra R.
Raya, Balaram
RajanBabu, T., V
ACS CATALYSIS, 2022, 12 (09) : 5094 - 5111
[33] CHIRAL SYNTHESIS VIA ORGANOBORANES .11. HYDROBORATION .82. ASYMMETRIC HYDROBORATION OF 1-HETEROARYLCYCLOALKENES WITH MONOISOPINOCAMPHEYLBORANE - SYNTHESIS OF TRANS-2-HETEROARYLCYCLOALKYL BORONATES AND DERIVED ALCOHOLS OF VERY HIGH ENANTIOMERIC PURITY
BROWN, HC
GUPTA, AK
PRASAD, JVNV
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (01) : 93 - 100
[34] Amplification of chirality by transition metal coordination:: synthesis of chiral allenes and allene manganese complexes of high enantiomeric purity.: Synthesis of methyl (R,E)-(-)-(2,4,5-tetradecatrienoate (pheromone of Acanthoscelides obtectus (say))
Franck-Neumann, M
Martina, D
Neff, D
TETRAHEDRON-ASYMMETRY, 1998, 9 (04) : 697 - 708
[35] Amplification of chirality by transition metal coordination: synthesis of chiral allenes and allene manganese complexes of high enantiomeric purity. Synthesis of methyl (R.E)-(-)-(2,4,5-tetradecatrienoate (pheromone of Acanthoscelides obtectus (say))
Franck-Neumann, M.
Martina, D.
Neff, D.
Tetrahedron: Asymmetry, 9 (04):
[36] THE USE OF (4R,5R)-DICARBOALKOXY-2-CHLORO-1,3,2-DIOXAPHOSPHOLANES AS NEW CHIRAL DERIVATIZING AGENTS FOR THE DETERMINATION OF ENANTIOMERIC PURITY OF ALCOHOLS BY P-31 NMR
BRUNEL, JM
PARDIGON, O
MAFFEI, M
BUONO, G
TETRAHEDRON-ASYMMETRY, 1992, 3 (10) : 1243 - 1246
[37] HYDROBORATION .68. CHIRAL SYNTHESIS VIA ORGANOBORANES .1. A SIMPLE PROCEDURE TO ACHIEVE PRODUCTS OF ESSENTIALLY 100-PERCENT OPTICAL PURITY IN HYDROBORATION OF ALKENES WITH MONOISOPINOCAMPHEYLBORANE - SYNTHESIS OF BORONIC ESTERS AND DERIVED PRODUCTS OF VERY HIGH ENANTIOMERIC PURITIES
BROWN, HC
SINGARAM, B
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (06) : 1797 - 1800
[38] CHIRAL SYNTHESIS VIA ORGANOBORANES .30. FACILE SYNTHESIS, BY THE MATTESON ASYMMETRIC HOMOLOGATION PROCEDURE, OF ALPHA-METHYL BORONIC ACIDS NOT AVAILABLE FROM ASYMMETRIC HYDROBORATION AND THEIR CONVERSION INTO THE CORRESPONDING ALDEHYDES, KETONES, CARBOXYLIC-ACIDS, AND AMINES OF HIGH ENANTIOMERIC PURITY
RANGAISHENVI, MV
SINGARAM, B
BROWN, HC
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10): : 3286 - 3294
[39] LARGE-SCALE SYNTHESIS OF THE BIFUNCTIONAL CHELATING AGENT 2-(P-NITROBENZYL)-1,4,7,10-TETRAAZACYCLODODECANE-N,N',N',N'''-TETRAACETIC ACID, AND THE DETERMINATION OF ITS ENANTIOMERIC PURITY BY CHIRAL CHROMATOGRAPHY
RENN, O
MEARES, CF
BIOCONJUGATE CHEMISTRY, 1992, 3 (06) : 563 - 569
[40] OPTIMIZATION OF ENANTIOCONTROL FOR CARBON-HYDROGEN INSERTION WITH CHIRAL DIRHODIUM(II) CARBOXAMIDATES - SYNTHESIS OF NATURAL DIBENZYLBUTYROLACTONE LIGNANS FROM 3-ARYL-1-PROPYL DIAZOACETATES IN HIGH OPTICAL PURITY
DOYLE, MP
PROTOPOPOVA, MN
ZHOU, QL
BODE, JW
SIMONSEN, SH
LYNCH, V
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21): : 6654 - 6655

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