An improved large scale synthesis of the Schollkopf chiral auxiliaries:: (2R)- and (2S)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine

被引：26

作者：

Chen, JX ^{[1
]}

Corbin, SP ^{[1
]}

Holman, NJ ^{[1
]}

机构：

[1] Albany Mol Res Inc, Syracuse Res Ctr, N Syracuse, NY 13212 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2005年 / 9卷 / 02期

关键词：

D O I：

10.1021/op049777t

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Syntheses of the Schollkopf chiral auxiliaries have been carried out on large scale in high overall yields from D- and L-valine. This method avoids the use of highly toxic phosgene or triphosgene, low-temperature reactions, and unstable intermediates.

引用

页码：185 / 187

页数：3

共 20 条

[1] Nonproteinogenic amino acids:: an efficient asymmetric synthesis of (S)-(-)-acromelobic acid and (S)-(-)-acromelobinic acid
Adamczyk, M
Akireddy, SR
Reddy, RE
[J]. TETRAHEDRON, 2002, 58 (34) : 6951 - 6963
[2] Practical synthesis of Schollkopf's bis-lactim ether chiral auxiliary: (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine
Bull, SD
Davies, SG
Moss, WO
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (02) : 321 - 327
[3] Asymmetric synthesis of alpha-methyl alpha-amino acids by diastereoselective alkylation of optically active 6-isopropyl-3-methyl-2,3-dihydro-6H-1,4-oxazin-2-ones
Chinchilla, R
Falvello, LR
Galindo, N
Najera, C
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (09): : 995 - 997
[4] Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones
Cledera, P
Avendaño, C
Menéndez, JC
[J]. TETRAHEDRON, 1998, 54 (40) : 12349 - 12360
[5] DENG C, 1981, ANGEW CHEM INT EDIT, V21, P798
[6] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS
DUTHALER, RO
[J]. TETRAHEDRON, 1994, 50 (06) : 1539 - 1650
[7] Ru(II)-catalyzed ring closing metathesis in stereoselective syntheses of constrained homoserine analogues
Hammer, K
Romming, C
Undheim, K
[J]. TETRAHEDRON, 1998, 54 (36) : 10837 - 10850
[8] 3-AMINO-2H-AZIRINES - SYNTHONS FOR ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACIDS IN HETEROCYCLE AND PEPTIDE-SYNTHESIS
HEIMGARTNER, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (03) : 238 - 264
[9] First asymmetric synthesis of chiral analogues of the novel immunosuppressant FTY720
Hinterding, K
Albert, R
Cottens, S
[J]. TETRAHEDRON LETTERS, 2002, 43 (45) : 8095 - 8097
[10] KOMPELLA UB, 1992, ADV DRUG DELIVER REV, V8, P115

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