Synthesis and Lewis acid-catalyzed nucleophilic substitution of chiral 1-alkoxyalkyl carboxylates

被引:44
作者
Matsutani, H
Ichikawa, S
Yaruva, J
Kusumoto, T
Hiyama, T
机构
[1] SAGAMI CHEM RES CTR,SAGAMIHARA,KANAGAWA 229,JAPAN
[2] TOKYO INST TECHNOL,RESOURCES UTILIZAT RES LAB,YOKOHAMA,KANAGAWA 226,JAPAN
关键词
OXOCARBENIUM ION INTERMEDIATE; OPTICALLY-ACTIVE ALCOHOLS; ASYMMETRIC-SYNTHESIS; PRACTICAL VERSION; DIOXANE ACETALS; 1,3-DIOXAN-4-ONES; MECHANISM; CENTERS;
D O I
10.1021/ja970153v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[No abstract available]
引用
收藏
页码:4541 / 4542
页数:2
相关论文
共 22 条
[11]  
JOHNSON WS, 1984, TETRAHEDRON LETT, V25, P3951, DOI 10.1016/0040-4039(84)80038-6
[12]  
Krow G.R., 1993, Organic Reactions, V43, P251
[13]   ACYCLIC STEREOSELECTION .52. ON THE MECHANISM OF LEWIS ACID MEDIATED NUCLEOPHILIC-SUBSTITUTION REACTIONS OF ACETALS [J].
MORI, I ;
ISHIHARA, K ;
FLIPPIN, LA ;
NOZAKI, K ;
YAMAMOTO, H ;
BARTLETT, PA ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) :6107-6115
[14]  
MUKAIYAMA T, 1987, SYNTHESIS-STUTTGART, P1043
[15]   DIRECT EVIDENCE FOR AN OXOCARBENIUM ION INTERMEDIATE IN THE ASYMMETRIC CLEAVAGE OF CHIRAL ACETALS [J].
SAMMAKIA, T ;
SMITH, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10998-10999
[16]   EVIDENCE FOR AN OXOCARBENIUM ION INTERMEDIATE IN LEWIS-ACID MEDIATED REACTIONS OF ACYCLIC ACETALS [J].
SAMMAKIA, T ;
SMITH, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7915-7916
[17]   ON THE PREPARATION OF OPTICALLY-ACTIVE SECONDARY ALCOHOLS FROM A 1,3-DIOXAN-4-ONE - SUBSTITUTION WITH ORGANOCOPPER REAGENTS [J].
SCHREIBER, SL ;
REAGAN, J .
TETRAHEDRON LETTERS, 1986, 27 (26) :2945-2948
[18]   PREPARATION OF OPTICALLY-ACTIVE ALCOHOLS FROM 1,3-DIOXAN-4-ONES - A PRACTICAL VERSION OF THE ASYMMETRIC-SYNTHESIS WITH NUCLEOPHILIC-SUBSTITUTION AT ACETAL CENTERS [J].
SEEBACH, D ;
IMWINKELRIED, R ;
STUCKY, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (02) :178-180
[19]   OPTICALLY-ACTIVE ALCOHOLS FROM 1,3-DIOXAN-4-ONES - A PRACTICAL VERSION OF ENANTIOSELECTIVE SYNTHESIS WITH NUCLEOPHILIC-SUBSTITUTION AT ACETAL CENTERS [J].
SEEBACH, D ;
IMWINKELRIED, R ;
STUCKY, G .
HELVETICA CHIMICA ACTA, 1987, 70 (02) :448-464
[20]  
Seebach D., 1986, MODEM SYNTHETIC METH, V4, P125