Chiral N-Phosphonyl Imine Chemistry: Asymmetric Synthesis of α-Alkyl β-Amino Ketones by Reacting Phosphonyl Imines with Ketone-Derived Enolates

被引：28

作者：

Ai, Teng ^{[1
]}

Han, Jianlin ^{[1
]}

Chen, Zhong-Xiu ^{[1
]}

Li, Guigen ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79401 USA

来源：

CHEMICAL BIOLOGY & DRUG DESIGN | 2009年 / 73卷 / 02期

关键词：

enolates; N-phosphonyl imines; phosphoramide; alpha-alkyl beta-amino ketones; SOLID-PHASE SYNTHESIS; MANNICH-TYPE REACTION; 1,3-AMINO ALCOHOLS; STEREOSELECTIVE-SYNTHESIS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CARBONYL-COMPOUNDS; FACILE SYNTHESIS; ALDEHYDES; SULFINIMINES;

D O I：

10.1111/j.1747-0285.2008.00771.x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of new chiral syn-alpha-branched beta-amino ketones has been synthesized by reacting chiral phosphonyl imines with ketone-derived enolates. The N-protection group on imine auxiliary was found to be crucial to the asymmetric induction. The absolute stereochemistry has been unambiguously determined by converting a product to a known sample.

引用

页码：203 / 208

页数：6

共 12 条

[1] Chiral N-phosphonyl imine chemistry:: Asymmetric addition of ketone-derived enolates for the synthesis of β-amino ketones
Han, Jianlin
Ai, Teng
Li, Guigen
SYNTHESIS-STUTTGART, 2008, (16): : 2519 - 2526
[2] Chiral N-phosphonyl imine chemistry: Asymmetric synthesis of α,β-diamino esters by reacting phosphonyl imines with glycine enolates
Ai, Teng
Li, Guigen
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (14) : 3967 - 3969
[3] Chiral N-phosphonyl imine chemistry: asymmetric additions of malonate-derived enolates to chiral N-phosphonyl imines for the synthesis of β-aminomalonates
Chen, Zhong-Xiu
Ai, Teng
Kaur, Parminder
Li, Guigen
TETRAHEDRON LETTERS, 2009, 50 (09) : 1079 - 1081
[4] Asymmetric synthesis of β'-amino-α-β-enones via addition of α,β-unsaturated ketone-derived enolates to chiral N-phosphonyl imines
Xiong, Yiwen
Mei, Haibo
Han, Jianlin
Li, Guigen
Pan, Yi
TETRAHEDRON LETTERS, 2014, 55 (15) : 2476 - 2479
[5] Chiral N-phosphonyl imine chemistry:: new reagents and their applications for asymmetric reactions
Kattuboina, Adiseshu
Li, Guigen
TETRAHEDRON LETTERS, 2008, 49 (10) : 1573 - 1577
[6] Chiral N-Phosphonylimine Chemistry: Asymmetric Synthesis of N-Phosphonyl β-Amino Weinreb Amides
Kaur, Parminder
Nguyen, Thao
Li, Guigen
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (06) : 912 - 916
[7] Asymmetric Hydrophosphylation of Chiral N-Phosphonyl Imines Provides an Efficient Approach to Chiral α-Amino Phosphonates
Kaur, Parminder
Wever, Walter
Rajale, Trideep
Li, Guigen
CHEMICAL BIOLOGY & DRUG DESIGN, 2010, 76 (04) : 314 - 319
[8] Asymmetric Catalytic N-Phosphonyl Imine Chemistry: The Use of Primary Free Amino Acids and Et2AlCN for Asymmetric Catalytic Strecker Reaction
Kaur, Parminder
Pindi, Suresh
Wever, Walter
Rajale, Trideep
Li, Guigen
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5144 - 5150
[9] Asymmetric Synthesis of α-Amino-1,3-dithianes via Chiral N-Phosphonyl Imine-Based Umpolung Reaction Without Using Chromatography and Recrystallization
Kattamuri, Padmanabha V.
Ai, Teng
Pindi, Suresh
Sun, Yinwei
Gu, Peng
Shi, Min
Li, Guigen
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (08): : 2792 - 2797
[10] Asymmetric synthesis of functionalized 2,3-dihydrobenzofurans using salicyl N-phosphonyl imines facilitated by group-assisted purification (GAP) chemistry
Rouh, Hossein
Tang, Yao
Zhang, Sai
Ali, Ahmed I. M.
Unruh, Daniel
Surowiec, Kazimierz
Li, Guigen
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (47) : 10319 - 10325

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