Mitsunobu Approach to the Synthesis of Optically Active α,α-Disubstituted Amino Acids

被引：73

作者：

Green, Jonathan E. ^{[1
,2
]}

Bender, David M. ^{[2
]}

Jackson, Stona ^{[2
]}

O'Donnell, Martin J. ^{[1
]}

McCarthy, James R. ^{[2
]}

机构：

[1] Indiana Univ Purdue Univ, Dept Chem & Chem Biol, Indianapolis, IN 46202 USA

[2] Eli Lilly & Co, Lilly Corp Ctr, Indianapolis, IN 46285 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 04期

关键词：

ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; STEREOSPECIFIC SYNTHESIS; ALKYL-ARYL; REAGENT; ALCOHOLS; DESIGN; ETHERS;

D O I：

10.1021/ol802325h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral tertiary alpha-hydroxy esters of known stereochemical configuration were transformed to a-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the a-carbon. Several alpha,alpha-disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

引用

页码：807 / 810

页数：4

共 50 条

[1] A facile synthesis of optically active β-amino-β-arylethylphosphonates by Mitsunobu reaction
Xu, CF
Yuan, CY
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (21) : 4410 - 4415
[2] Convenient synthesis of optically pure α-mono and α,α-disubstituted β-amino acids
Lee, HS
Park, JD
Kim, DH
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (04) : 467 - 472
[3] An asymmetric synthesis of optically pure α,α-disubstituted amino aldehydes, α,α-disubstituted amino acids, and sterically demanding dipeptides
Wenglowsky, S
Hegedus, LS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (48) : 12468 - 12473
[4] CHEMOENZYMATIC SYNTHESIS OF OPTICALLY-ACTIVE ALPHA,ALPHA-DISUBSTITUTED ALPHA-AMINO-ACIDS
LIU, WG
RAY, P
BENEZRA, SA
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (05): : 553 - 559
[5] CHEMOENZYMATIC SYNTHESIS OF OPTICALLY-ACTIVE 2,2-DISUBSTITUTED 2-AMINO ACIDS
LIU, WG
RAY, P
BENEZRA, SA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 207 - BIOT
[6] Synthesis of optically active bis-a-amino acids
Cao, Fei
Li, Zhen-Jiang
Zhou, Hua
Wei, Ping
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (10) : 1344 - 1352
[7] Synthesis of optically active alpha,alpha-disubstituted amino aldehydes.
Wenglowsky, S
Hegedus, LS
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 214 : 220 - ORGN
[8] Synthesis of optically active silicon-containing amino acids
Peng, HS
Zong, MH
Li, N
Wang, JF
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (02) : 115 - 119
[9] A novel synthesis of optically active alpha-amino acids
Demir, AS
PURE AND APPLIED CHEMISTRY, 1997, 69 (01) : 105 - 108
[10] STERIC COURSE OF SYNTHESIS OF AMINOXY ACIDS FROM OPTICALLY ACTIVE AMINO ACIDS
LIBEREK, B
CUPRYSZA.C
ROCZNIKI CHEMII, 1971, 45 (04): : 677 - &

← 1 2 3 4 5 →