Facile synthesis of optically pure 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines

被引：57

作者：

Ruano, JLG ^{[1
]}

Alemán, J ^{[1
]}

Soriano, JF ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Dept Quim Organ, E-28049 Madrid, Spain

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 05期

关键词：

D O I：

10.1021/ol027464h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical. purity employing conventional methods (TFA and Raney-Ni, respectively).

引用

页码：677 / 680

页数：4

共 50 条

[41] SYNTHESIS OF OPTICALLY-ACTIVE 2-ARYLALKANOIC ACIDS BY THE USE OF 1,2-REARRANGEMENT OF THE ARYL GROUP
TSUCHIHASHI, G
MITAMURA, S
KITAJIMA, K
KOBAYASHI, K
TETRAHEDRON LETTERS, 1982, 23 (51) : 5427 - 5430
[42] Facile Synthesis of Carbazoles via a Tandem Iodocyclization with 1,2-Alkyl Migration and Aromatization
Wang, Jia
Zhu, Hai-Tao
Qiu, Yi-Feng
Niu, Yuan
Chen, Si
Li, Ying-Xiu
Liu, Xue-Yuan
Liang, Yong-Min
ORGANIC LETTERS, 2015, 17 (12) : 3186 - 3189
[43] 1H-4,5,6,7-tetrahydro-1,3-diazepines.: Part I:: Synthesis, spectral and chemical properties of 1,2-diaryl derivatives
Hedrera, ME
Perillo, IA
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (06) : 1431 - 1438
[44] Facile synthesis of diastereoisomerically and optically pure 2-substituted hexahydro-1H-pyrrolizin-3-ones
Siegrist, R
Baumgartner, C
Seiler, P
Diederich, F
HELVETICA CHIMICA ACTA, 2005, 88 (08) : 2250 - 2261
[45] SYNTHESIS OF 2-ALKYL(ARYL)-CIS-1-THIADECALIN
VOLYNSKII, NP
ZEGELMAN, LA
SMIRNOV, MB
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (02): : 341 - 367
[46] SYNTHESIS OF 2-ALKYL(ARYL)-CIS-1-THIAHYDRINDANES
VOLYNSKII, NP
ZEGELMAN, LA
SMIRNOV, MB
BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1988, 37 (10): : 2118 - 2122
[47] SYNTHESIS OF ALKYL AND ARYL SUBSTITUTED BENZO[h]NAPHTHO[1,2-b][1,6]NAPHTHYRIDINES
Prabha, K.
Prasad, K. J. Rajendra
SYNTHETIC COMMUNICATIONS, 2012, 42 (15) : 2277 - 2289
[48] REGIOSELECTIVE SYNTHESIS OF 1-ALKYL-1-PHENYLHYDRAZINES, 2-ALKYL-1-PHENYLHYDRAZINES, AND 1,2-DIALKYL-1-PHENYLHYDRAZINES
BARLUENGA, J
MERINO, I
VINA, S
PALACIOS, F
SYNTHESIS-STUTTGART, 1990, (05): : 398 - 400
[49] SYNTHESIS AND STRUCTURE DETERMINATION OF GEOMETRIC ISOMERS OF 1-ARYL-2-ETHYL-1,2-DIPHENYLETHYLENES BY H-1-NMR SPECTROSCOPY
SOHAR, P
ABRAHAM, G
SCHNEIDER, G
HORVATH, T
FUGGERTH, E
ACTA CHIMICA ACADEMIAE SCIENTARIUM HUNGARICAE, 1979, 100 (1-4): : 69 - 74
[50] INTERNAL-ROTATION AND CONFORMATIONAL PREFERENCES IN 1,2-DIARYL DERIVATIVES OF 1,1,2,2-TETRACHLOROETHANE - A H-1 DNMR AND X-RAY STRUCTURAL STUDY
ANTOLINI, L
FOLLI, U
MUCCI, A
SBARDELLATI, S
TADDEI, F
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1994, (05): : 1107 - 1114

← 1 2 3 4 5 →