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
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
收藏
页码:185 / 187
页数:3
相关论文
共 20 条
[1]   Nonproteinogenic amino acids:: an efficient asymmetric synthesis of (S)-(-)-acromelobic acid and (S)-(-)-acromelobinic acid [J].
Adamczyk, M ;
Akireddy, SR ;
Reddy, RE .
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 [J].
Bull, SD ;
Davies, SG ;
Moss, WO .
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 [J].
Chinchilla, R ;
Falvello, LR ;
Galindo, N ;
Najera, C .
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 [J].
Cledera, P ;
Avendaño, C ;
Menéndez, JC .
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 [J].
DUTHALER, RO .
TETRAHEDRON, 1994, 50 (06) :1539-1650
[7]   Ru(II)-catalyzed ring closing metathesis in stereoselective syntheses of constrained homoserine analogues [J].
Hammer, K ;
Romming, C ;
Undheim, K .
TETRAHEDRON, 1998, 54 (36) :10837-10850
[8]   3-AMINO-2H-AZIRINES - SYNTHONS FOR ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACIDS IN HETEROCYCLE AND PEPTIDE-SYNTHESIS [J].
HEIMGARTNER, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (03) :238-264
[9]   First asymmetric synthesis of chiral analogues of the novel immunosuppressant FTY720 [J].
Hinterding, K ;
Albert, R ;
Cottens, S .
TETRAHEDRON LETTERS, 2002, 43 (45) :8095-8097
[10]  
KOMPELLA UB, 1992, ADV DRUG DELIVER REV, V8, P115