Enantioselective addition of diethylzinc to aldehydes catalyzed by a new chiral β-amino alcohol derived from D-mannitol

被引:55
作者
Cho, BT [1 ]
Chun, YS [1 ]
机构
[1] Hallym Univ, Dept Chem, Chunchon 200702, South Korea
关键词
D O I
10.1016/S0957-4166(98)00143-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A new chiral beta-dialkylamino alcohol 1 prepared from D-mannitol has been used as a highly effective chiral catalyst for the enantioselective addition of diethylzinc to unhindered aliphatic aldehydes to afford the product alcohols in up to 94% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.
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收藏
页码:1489 / 1492
页数:4
相关论文
共 25 条
[1]   SYNTHETIC NUCLEOSIDES .55. FACILE DISPLACEMENT REACTIONS IN D-MANNITOL SERIES .2. SYNTHESIS OF SOME 3-AMINOHEXITOLS [J].
BAKER, BR ;
HAINES, AH .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (02) :442-&
[2]  
BELLICZEY J, 1997, TETRAHEDRON-ASYMMETR, V8, P1529
[3]   CATALYZED ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES [J].
BOLM, C ;
SCHLINGLOFF, G ;
HARMS, K .
CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05) :1191-1203
[4]  
CHO BT, 1994, TETRAHEDRON LETT, V35, P4115
[5]   PREPARATION OF 1,2-ISOPROPYLIDENE-5-DEOXY-5-DIALKYLAMINO-ALPHA-D-XYLOFURANOSE DERIVATIVES AS CHIRAL CATALYSTS FOR ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES [J].
CHO, BT ;
KIM, N .
SYNTHETIC COMMUNICATIONS, 1995, 25 (02) :167-175
[6]  
CHO BT, 1994, B KOR CHEM SOC, V15, P931
[7]  
Cho BT, 1996, B KOR CHEM SOC, V17, P1
[8]   Catalytic enantioselective reactions .9. 1,2-O-isopropylidene-5-deoxy-5-N,N-dialkyl (or -N-monoalkyl)amino-alpha-D-xylofuranose derivatives as highly-effective chiral catalysts for enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes [J].
Cho, BT ;
Kim, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (24) :2901-2907
[9]   Catalytic enantioselective reactions .7. Synthesis of new beta-aminoalcohols derived from alpha-D-glucose as chiral catalysts for the catalytic enantioselective addition of diethylzinc to aldehydes [J].
Cho, BT ;
Kim, N .
SYNTHETIC COMMUNICATIONS, 1996, 26 (05) :855-865
[10]   Catalytic enantioselective reactions .8. Catalytic enantioselective addition of diethylzinc to aldehydes using (2S,3S)-(-)-1,4-diamino-2,3-butanediol derivatives as chiral catalysts [J].
Cho, BT ;
Kim, N .
SYNTHETIC COMMUNICATIONS, 1996, 26 (12) :2273-2280