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Acyclic stereoselective boron alkylation reactions for the asymmetric synthesis of β-substituted α-amino acid derivatives
被引:42
作者
:
O'Donnell, MJ
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA
Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA
O'Donnell, MJ
[
1
]
Cooper, JT
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA
Cooper, JT
Mader, MM
论文数:
0
引用数:
0
h-index:
0
机构:
Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA
Mader, MM
机构
:
[1]
Indiana Univ Purdue Univ, Dept Chem, Indianapolis, IN 46202 USA
[2]
Eli Lilly & Co, Lilly Res Labs, Indianapolis, IN 46285 USA
来源
:
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
|
2003年
/ 125卷
/ 09期
关键词
:
D O I
:
10.1021/ja0298794
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Optically active syn- or anti-β-substituted-α-amino acid derivatives are prepared in 94 to ≥99% ee and 66-98% ds by reaction of the Schiff base acetate of glycine tert-butyl ester with chiral, nonracemic B-alkyl-9-BBN derivatives in the presence of the Cinchona alkaloid, cinchonidine (CdOH) or cinchonine (CnOH), base, and lithium chloride. Copyright © 2003 American Chemical Society.
引用
收藏
页码:2370 / 2371
页数:2
相关论文
共 24 条
[21]
Asymmetric synthesis of α,β-dialkyl-α-phenylalanines via direct alkylation of a chiral alanine derivative with racemic α-alkylbenzyl bromides.: A case of high enantiomer differentiation at room temperature
[J].
Soloshonok, VA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Soloshonok, VA
;
Tang, XJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Tang, XJ
;
Hruby, VJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Hruby, VJ
;
Van Meervelt, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Van Meervelt, L
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ORGANIC LETTERS,
2001,
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(03)
:341
-343
[22]
Large-scale asymmetric synthesis of novel sterically constrained 2′,6′-dimethyl- and α,2′,6′-trimethyltyrosine and -phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine
[J].
Soloshonok, VA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Soloshonok, VA
;
Tang, XJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Tang, XJ
;
Hruby, VJ
论文数:
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引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Hruby, VJ
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TETRAHEDRON,
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Tamura O, 2000, SYNLETT, P1553
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THE STEREOCHEMISTRY OF KETONIZATION .8. ACYCLIC ENOLS
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ZIMMERMAN, HE
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引用数:
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h-index:
0
ZIMMERMAN, HE
;
CHANG, WH
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引用数:
0
h-index:
0
CHANG, WH
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1959,
81
(14)
:3634
-3643
←
1
2
3
→
共 24 条
[21]
Asymmetric synthesis of α,β-dialkyl-α-phenylalanines via direct alkylation of a chiral alanine derivative with racemic α-alkylbenzyl bromides.: A case of high enantiomer differentiation at room temperature
[J].
Soloshonok, VA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Soloshonok, VA
;
Tang, XJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Tang, XJ
;
Hruby, VJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Hruby, VJ
;
Van Meervelt, L
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Van Meervelt, L
.
ORGANIC LETTERS,
2001,
3
(03)
:341
-343
[22]
Large-scale asymmetric synthesis of novel sterically constrained 2′,6′-dimethyl- and α,2′,6′-trimethyltyrosine and -phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine
[J].
Soloshonok, VA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Soloshonok, VA
;
Tang, XJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Tang, XJ
;
Hruby, VJ
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Univ Arizona, Dept Chem, Tucson, AZ 85721 USA
Hruby, VJ
.
TETRAHEDRON,
2001,
57
(30)
:6375
-6382
[23]
Tamura O, 2000, SYNLETT, P1553
[24]
THE STEREOCHEMISTRY OF KETONIZATION .8. ACYCLIC ENOLS
[J].
ZIMMERMAN, HE
论文数:
0
引用数:
0
h-index:
0
ZIMMERMAN, HE
;
CHANG, WH
论文数:
0
引用数:
0
h-index:
0
CHANG, WH
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1959,
81
(14)
:3634
-3643
←
1
2
3
→