HIGHLY STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF THE TITANIUM ENOLATE OF A CHIRAL 2-PYRIDYLTHIOESTER WITH CHIRAL IMINES

被引：21

作者：

ANNUNZIATA, R

BENAGLIA, M

CHIOVATO, A

CINQUINI, M

COZZI, F

机构：

[1] UNIV MILAN,CTR CNR,I-20133 MILAN,ITALY

[2] UNIV MILAN,DIPARTIMENTO CHIM ORGAN & IND,I-20133 MILAN,ITALY

来源：

TETRAHEDRON | 1995年 / 51卷 / 36期

关键词：

D O I：

10.1016/0040-4020(95)00574-R

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the titanium enolate of a 2-pyridylthioester derived from (R)-3-hydroxybutyric acid with chiral imines affords 3,3'-anti-3,4-trans configurated beta-lactams in a highly selective fashion. The methodology has been applied to the synthesis of a precursor of the carbapenem antibiotic 1 beta-methylthienamycin.

引用

收藏

页码：10025 / 10032

页数：8

相关论文

共 29 条

[1] SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES - INFLUENCE OF THE IMINE STRUCTURE ON THE TRANS/CIS STEREOSELECTIVITY [J].

ANNUNZIATA, R ;

BENAGLIA, M ;

CINQUINI, M ;

COZZI, F ;

PONZINI, F ;

RAIMONDI, L .

TETRAHEDRON, 1994, 50 (09) :2939-2948

[2] STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS WITH IMINES [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

COZZI, PG .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4155-4162

[3] STEREOSELECTIVE SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYL THIOESTERS WITH IMINES BEARING A CHIRAL AUXILIARY [J].

ANNUNZIATA, R ;

BENAGLIA, M ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L .

TETRAHEDRON, 1994, 50 (31) :9471-9486

[4] STEREOSELECTIVE SYNTHESIS OF AZETIDIN-2-ONES, PRECURSORS OF BIOLOGICALLY-ACTIVE SYN-3-AMINO-2-HYDROXYBUTANOIC ACIDS [J].

ANNUNZIATA, R ;

BENAGLIA, M ;

CINQUINI, M ;

COZZI, F ;

PONZINI, F .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4746-4748

[5]

ANNUNZIATA R, 1993, GAZZ CHIM ITAL, V123, P181

[6]

BROWN MJ, 1989, HETEROCYCLES, V29, P2225

[7] STEREOSPECIFIC SYNTHESIS OF A CHIRAL INTERMEDIATE FOR THE PREPARATION OF THIENAMYCIN, PENEMS, AND CARBAPENEMS - USE OF THE NITRO-GROUP AS A HYDROXY PROTECTING GROUP [J].

CAINELLI, G ;

PANUNZIO, M ;

BASILE, T ;

BONGINI, A ;

GIACOMINI, D ;

MARTELLI, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2637-2642

[8] A STEREOSELECTIVE SYNTHESIS OF A KEY 1-BETA-METHYLCARBAPENEM INTERMEDIATE VIA A DIASTEREOSELECTIVE DECARBOXYLATION [J].

CHOI, WB ;

CHURCHILL, HRO ;

LYNCH, JE ;

THOMPSON, AS ;

HUMPHREY, GR ;

VOLANTE, RP ;

REIDER, PJ ;

SHINKAI, I .

TETRAHEDRON LETTERS, 1994, 35 (15) :2275-2278

[9] MILD AND CONVENIENT ONE-POT SYNTHESIS OF BETA-LACTAMS BY CONDENSATION OF TITANIUM ENOLATES OF 2-PYRIDYLTHIOESTERS WITH IMINES [J].

CINQUINI, M ;

COZZI, F ;

COZZI, PG ;

CONSOLANDI, E .

TETRAHEDRON, 1991, 47 (41) :8767-8774

[10] ENANTIOSELECTIVE MICHAEL REACTIONS - DIASTEREOSELECTIVE REACTIONS OF CHLOROTITANIUM ENOLATES OF CHIRAL N-ACYLOXAZOLIDINONES WITH REPRESENTATIVE ELECTROPHILIC OLEFINS [J].

EVANS, DA ;

BILODEAU, MT ;

SOMERS, TC ;

CLARDY, J ;

CHERRY, D ;

KATO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5750-5752