RITTER REACTION ON TERPENOIDS .3. STEREOSPECIFIC PREPARATION OF BICYCLIC [3.3.1] SUBSTITUTED PIPERIDINES

被引：30

作者：

SAMANIEGO, WN

BALDESSARI, A

PONCE, MA

RODRIGUEZ, JB

GROS, EG

CARAM, JA

MARSCHOFF, CM

机构：

[1] UNIV BUENOS AIRES,FAC CIENCIAS EXACTAS,DEPT QUIM ORGAN,RA-1428 BUENOS AIRES,DF,ARGENTINA

[2] INST INVEST FIS QUIM TEORICAS & APLICADAS,DIV ELECTROQUIM,RA-1900 LA PLATA,BUENOS AIRES,ARGENTINA

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 38期

关键词：

D O I：

10.1016/0040-4039(94)88200-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of chiral monoterpenes with different nitrile compounds in the presence of perchloric acid affords (1S,5R,8R) 8-alkyl(aryl)-2-alkyl(aryl)-2,4,4,8-tetramethyl-3-azabicyclo[3.3.1]non-2-ene or the corresponding (1R,5S,8S) enantiomer, The respective free imines yield optically pure piperidine derivatives when treated with reducing agents (NaBH4, NaCNBH3).

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页码：6967 / 6970

页数：4

相关论文

共 15 条

[1] ARISTOTELINE, A NOVEL INDOLE ALKALOID - X-RAY STRUCTURAL DETERMINATION [J].

ANDERSON, BF ;

ROBERTSON, GB ;

AVEY, HP ;

DONOVAN, WF ;

BICK, IRC ;

BREMNER, JB ;

FINNEY, AJT ;

PRESTON, NW ;

GALLAGHER, RT ;

RUSSELL, GB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (13) :511-512

[2] ARISTOTELINE AND ARISTOTELONE, UNUSUAL INDOLE ALKALOIDS FROM ARISTOTELIA-CHILENSIS [J].

BHAKUNI, DS ;

SILVA, M ;

MATLIN, SA ;

SAMMES, PG .

PHYTOCHEMISTRY, 1976, 15 (04) :574-575

[3] ARISTOTELINONE AND SERRATOLINE - NEW INDOLE ALKALOIDS FROM ARISTOTELIA-SERRATA WRB OLIVER [J].

BICK, IRC ;

HAI, MA ;

PRESTON, NW ;

GALLAGHER, RT .

TETRAHEDRON LETTERS, 1980, 21 (06) :545-546

[4] RITTER REACTIONS .3. A SIMPLE ENTRY INTO THE 3-AZATRICYCLO[5.3.1.0/4,9]UNDECANE SYSTEM [J].

BISHOP, R ;

HAWKINS, SC ;

IBANA, IC .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (02) :427-430

[5] RITTER REACTIONS .5. FURTHER INVESTIGATION OF THE 3-AZATRICYCLO[5.3.1.04,9]UNDEC-2-ENE SYSTEM [J].

BONG, ICC ;

UNG, AT ;

CRAIG, DC ;

SCUDDER, ML ;

BISHOP, R .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1989, 42 (11) :1929-1937

[6]

CARAM J, 1984, Z NATURFORSCH B, V39, P972

[7] ON THE UNUSUAL HYDROLYSIS REACTION OF 8-ACETAMIDO-2,4,4,8-TETRAMETHYL-3-AZANIUM-BICYCLO[3.3.1]NON-2-ENE PERCHLORATE [J].

CARAM, JA ;

RIVERO, BE ;

PIRO, OE ;

GROS, EG ;

MARSCHOFF, CM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1990, 68 (02) :334-338

[8]

HARADA K, 1970, CHEM CARBON NITROGEN, P276

[9]

Johnson F., 1966, ADVANCES HETEROCYCLI, V6,, P95

[10]

Krimen L. I., 1969, ORG REACTIONS, V17, P213, DOI DOI 10.1002/0471264180.0R017.03