Improved practical asymmetric synthesis of α-alkylmandelic acids utilizing highly diastereoselective alkylation of 5-aryl-2-(1-naphthyl)-1,3-dioxolan-4-ones

被引:16
作者
Misaki, Tomonori [1 ]
Ureshino, Satoko [1 ]
Nagase, Ryohei [1 ]
Oguni, Yumiko [1 ]
Tanabe, Yoo [1 ]
机构
[1] Kwansei Gakuin Univ, Sch Sci & Technol, Dept Chem, Sanda, Hyogo 6691337, Japan
关键词
D O I
10.1021/op050263j
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A practical method for the synthesis of optically pure alpha-alkylmandelic acids 1 is described. The present improved robust method involved two reactions: a mild, convenient, stereoselective preparation of chiral cis-5-aryl-2-(1-naphthyl)-1,3-dioxolan- 4-ones, 9a-c, and highly diastereoselective alkylation of 9a-c, followed by the hydrolysis.
引用
收藏
页码:500 / 504
页数:5
相关论文
共 50 条
[21]   One-pot synthesis of (3R)-hydroxy-beta-lactams via enolates of 2-tert-butyl-1,3-dioxolan-4-ones .1. [J].
Barbaro, G ;
Battaglia, A ;
Guerrini, A ;
Bertucci, C .
TETRAHEDRON-ASYMMETRY, 1997, 8 (15) :2527-2531
[22]   1,3-DIOXOLANE C-NUCLEOSIDES - ASYMMETRIC-SYNTHESIS OF 4 STEREOISOMERS OF 2-[2-(HYDROXYMETHYL)-1,3-DIOXOLAN-5-YL)]-1,3-THIAZOLE-4-CARBOXAMIDE [J].
DU, JF ;
QU, FC ;
LEE, DW ;
NEWTON, MG ;
CHU, CK .
TETRAHEDRON LETTERS, 1995, 36 (45) :8167-8170
[23]   (4R,5S)-1,5-dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative:: practical asymmetric synthesis of α-amino acids [J].
Guillena, G ;
Nájera, C .
TETRAHEDRON-ASYMMETRY, 1998, 9 (07) :1125-1129
[24]   2-STEP STEREOSELECTIVE CONVERSION OF 5-MONOSUBSTITUTED 1,3-DIOXOLAN-4-ONES INTO SELECTIVELY PROTECTED 2,3-ERYTHRO-1,2,3-TRIOLS - A ROUTE TO POLYHYDROXYLATED MOLECULES [J].
UNTERSTELLER, E ;
XIN, YC ;
SINAY, P .
TETRAHEDRON LETTERS, 1994, 35 (16) :2537-2540
[25]   Synthesis of 2-aryl-4-hydroxy-5-thio substituted 1,3-thiazin-6-ones via sulfenylation of 2-aryl-4-hydroxy-[1,3]thiazin-6-ones with sulfenyl chlorides [J].
Prasad, JVNV .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (06) :1599-1603
[26]   Synthesis of 5-Amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)- 2,3-dihydro-1H-pyrrol-3-ones* [J].
Yu. M. Volovenko ;
T. A. Volovnenko ;
A. V. Tverdokhlebov ;
I. G. Ryabokon' .
Russian Journal of Organic Chemistry, 2001, 37 :1323-1329
[27]   Synthesis of 5-amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)2,3-dihydro-1H-pyrrol-3-ones [J].
Volovenko, YM ;
Volovnenko, TA ;
Tverdokhlebov, AV ;
Ryabokon, IG .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 37 (09) :1323-1329
[28]   (4R,5S)-1,5-Dimethyl-4-phenylimidazolidin-2-one as a chiral auxiliary for the diastereoselective alkylation of a new iminic glycine derivative: practical asymmetric synthesis of a-amino acids [J].
Guillena, G. ;
Najera, C. .
Tetrahedron: Asymmetry, 9 (07)
[29]   ASYMMETRIC SYNTHESIS VIA HETEROCYCLIC INTERMEDIATES .1. ASYMMETRIC SYNTHESIS OF ALPHA-ALKYL-ALPHA-AMINOCARBOXYLIC ACIDS BY ALKYLATION OF 1-CHIRAL-SUBSTITUTED 2-IMIDAZOLIN-5-ONES [J].
SCHOLLKOPF, U ;
HAUSBERG, HH ;
HOPPE, I ;
SEGAL, M ;
REITER, U .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1978, 17 (02) :117-119
[30]   Synthesis of 2′-aryl-3-N10-[(acetylamino)-1,3-thiazolidin-4-ones] and 5′-arylidine-2-aryl-3-N10-[(acetylamino)-1,3-thiazolidin-4-ones] and their antimicrobial and diuretic activities [J].
Yadav, Ritu ;
Jain, Vikrant ;
Srivastava, S. D. ;
Srivastava, Soumya ;
Srivastava, S. K. .
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 2009, 86 (05) :537-543