(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine-Catalyzed Efficient Stereoselective Michael Addition of Cyclohexanone and Cyclopentanone to Nitroolefins

被引：12

作者：

Singh, Kamal Nain ^{[1
]}

Singh, Paramjit ^{[1
]}

Kaur, Amarjit ^{[1
]}

Singh, Pushpinder ^{[1
]}

Sharma, Sandeep Kumar ^{[1
]}

Khullar, Sadhika ^{[2
]}

Mandal, Sanjay K. ^{[2
]}

机构：

[1] Panjab Univ, Dept Chem, Chandigarh 160014, India

[2] Indian Inst Sci Educ & Res, Dept Chem Sci, Sect 81, Mohali 140306, Punjab, India

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 10期

关键词：

Michael addition reaction; organocatalyst; amino sulfoxide; nitroolefins; ketones; ENANTIOSELECTIVE CONJUGATE ADDITION; CYCLIC-KETONES; NITRO-MICHAEL; BIFUNCTIONAL ORGANOCATALYSTS; METHYL-ETHER; ALDEHYDES; THIOUREA; AMINE; CATALYSTS; ENAMINE;

D O I：

10.1055/s-0032-1316917

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(2S)-2-[(Phenylsulfinyl)methyl]pyrrolidine, derived from L-proline, has been demonstrated as an efficient organocatalyst for the asymmetric Michael addition of cyclohexanone and cyclopentanone to beta-nitrostyrenes. This pyrrolidine-based catalyst bearing a sulfoxide moiety was used to synthesize various gamma-nitro carbonyl compounds in high yield (up to 97%) with excellent stereoselectivity (up to >99:1 dr and >99% ee) without the use of any additive.

引用

页码：1406 / 1413

页数：8

共 50 条

[21] An efficient stereoselective synthesis of (2S,3S)-3-hydroxy-2-phenylpiperidine
Bodas, MS
Upadhyay, PK
Kumar, P
TETRAHEDRON LETTERS, 2004, 45 (05) : 987 - 988
[22] (S)-benzyl 2-(6-methyl-2-pyridylaminocarbonyl)pyrrolidine-1-carboxylate
Kang, Tai-Ran
Ng, Seik Weng
He, Long
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3847 - U3356
[23] (2S,SR)-tert-butyl 2-(p-tolylsulfinylacetyl)-pyrrolidine-1-carboxylate
Toscano, RA
Carrasco, A
Ortiz, B
Sánchez-Obregón, R
Walls, F
Yuste, F
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1999, 55 : 1605 - 1607
[24] (2S)-Methyl 2-(4-chlorobenzenesulfonamido)-4-(methylsulfanyl)butanoate
Syed, Tayyaba
Hameed, Shahid
Jones, Peter G.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1348 - U2477
[25] ENANTIOFACE-DIFFERENTIATING (ASYMMETRIC) ADDITION OF ALKYLLITHIUM TO ALDEHYDES BY USING (2S, 2'S)-2-HYDROXYMETHYL-1-[(1-METHYLPYRROLIDIN-2-YL)METHYL]-PYRROLIDINE AS CHIRAL LIGAND
MUKAIYAMA, T
SOAI, K
KOBAYASHI, S
CHEMISTRY LETTERS, 1978, (02) : 219 - 222
[26] An efficient synthesis of (2S)-2-[4-((1R, 2S)-2-hydroxycyclopentylmethyl)phenyl]propionic acid
Mandai, T
Yamakawa, T
SYNLETT, 2000, (06) : 862 - 864
[27] A Concise Synthesis of (S)-2-(Fluorodiphenylmethyl) pyrrolidine: A Novel Organocatalyst for the Stereoselective Epoxidation of α,β-Unsaturated Aldehydes
Sparr, Christof
Tanzer, Eva-Maria
Bachmann, Julia
Gilmour, Ryan
SYNTHESIS-STUTTGART, 2010, (08): : 1394 - 1397
[28] Structure of (2S)-1-[(2R)-2,4-diphenyl-4-oxobutylideneamino]-2-(methoxymethyl) pyrrolidine
Dianez, MJ
Estrada, MD
Lopez-Castro, A
Perez-Garrido, S
ZEITSCHRIFT FUR KRISTALLOGRAPHIE, 1997, 212 (12): : 878 - 880
[29] Stereoselective Michael addition of thiophenols, amino acids and hydrazoic acid to (2S)-hydroxymethyl-dihydropyridone as a convenient route to novel azasugar derivatives
Koulocheri, SD
Magiatis, P
Skaltsounis, AL
Haroutounian, SA
TETRAHEDRON, 2000, 56 (33) : 6135 - 6141
[30] (2S,4S,SFc)-2-[2-(diphenylthiophosphinoyl)ferrocenyl]-4-methoxy-methyl-1,3-dioxane
Daran, Jean-claude
Manoury, Eric
Routaboul, Lucie
Rivas, Frederic
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2006, 62 : M378 - M380

← 1 2 3 4 5 →