STEREOSPECIFIC FRIEDEL-CRAFTS ALKYLATION OF BENZENE WITH 4-MESYLOXY-L-PROLINES - A NEW SYNTHESIS OF 4-PHENYLPROLINES

被引：36

作者：

KRONENTHAL, DR

MUELLER, RH

KUESTER, PL

KISSICK, TP

JOHNSON, EJ

机构：

[1] Squibb Chemical Development P. O., Princeton, NJ 08540

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(00)88775-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of benzene with cis- and trans-N-benzoyl-4-mesyloxy-L-proline (11 and 12) in the presence of AlCl3 stereospecifically produces the corresponding trans- and cis-4-phenylproline derivatives. © 1990.

引用

页码：1241 / 1244

页数：4

共 14 条

[1] SYNTHESIS OF OPTICALLY-ACTIVE CHLORO ALKANOIC ESTERS [J].

AZZENA, U ;

DELOGU, G ;

MELLONI, G ;

PICCOLO, O .

TETRAHEDRON LETTERS, 1989, 30 (34) :4555-4558

[2] A STEREOSPECIFIC FRIEDEL-CRAFTS REACTION . ALKYLATION OF BENZENE WITH GAMMA-VALEROLACTONE [J].

BRAUMAN, JI ;

PANDELL, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5421-&

[3]

DRAHOWZAL FA, 1964, FRIEDEL CRAFTS RELAT, V2, P646

[4] ELECTROPHILIC AROMATIC-SUBSTITUTION .12. STEREOSELECTIVE ALKYLATION OF AROMATIC-COMPOUNDS WITH THREONINE TRIFLUOROMETHANESULFONATES [J].

EFFENBERGER, F ;

WEBER, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (02) :142-143

[5] SYNTHESIS OF 4-SUBSTITUTED PROLINES AS CONFORMATIONALLY CONSTRAINED AMINO-ACID ANALOGS [J].

KOSKINEN, AMP ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (08) :1859-1866

[6] ANGIOTENSIN-CONVERTING ENZYME-INHIBITORS - MERCAPTAN, CARBOXYALKYL DIPEPTIDE, AND PHOSPHINIC ACID INHIBITORS INCORPORATING 4-SUBSTITUTED PROLINES [J].

KRAPCHO, J ;

TURK, C ;

CUSHMAN, DW ;

POWELL, JR ;

DEFORREST, JM ;

SPITZMILLER, ER ;

KARANEWSKY, DS ;

DUGGAN, M ;

ROVNYAK, G ;

SCHWARTZ, J ;

NATARAJAN, S ;

GODFREY, JD ;

RYONO, DE ;

NEUBECK, R ;

ATWAL, KS ;

PETRILLO, EW .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (06) :1148-1160

[7] ASYMMETRIC INDUCTION IN FRIEDEL-CRAFTS REACTION WITH (+)-1,2-EPOXYBUTANE AND (-)-2-CHLORO-1-BUTANOL [J].

NAKAJIMA, T ;

NAKAMOTO, Y ;

SUGA, S .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1975, 48 (03) :960-965

[8]

OLAH G, 1963, FRIEDEL CRAFTS RELAT, V1, P40

[9] ALKYLATION OF AROMATIC-COMPOUNDS WITH OPTICALLY-ACTIVE LACTIC-ACID DERIVATIVES - SYNTHESIS OF OPTICALLY PURE 2-ARYLPROPIONIC ACID AND ESTERS [J].

PICCOLO, O ;

SPREAFICO, F ;

VISENTIN, G ;

VALOTI, E .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3945-3946

[10] BICYCLIC BASES - SYNTHESIS AND NUCLEAR MAGNETIC RESONANCE INVESTIGATION OF SOME CHIRAL 2-OXA-5-AZABICYCLO[2.2.1]HEPTANE DERIVATIVES [J].

PORTOGHESE, PS ;

TURCOTTE, JG .

TETRAHEDRON, 1971, 27 (05) :961-+

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