Asymmetric synthesis of unusual fused tricyclic β-lactam structures via aza-cycloadditions/ring closing metathesis

被引:35
作者
Alcaide, B [1 ]
Almendros, P
Alonso, JM
Redondo, MC
机构
[1] Univ Complutense Madrid, Dept Quim Organ 1, Fac Quim, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
D O I
10.1021/jo026112l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Conveniently substituted bis-beta-lactams, pyrrolidinyl-beta-lactams, and piperidinyl-beta-lactams undergo ring-closing methatesis using Grubbs' carbene, Cl-2(Cy3P)(2)Ru = CHPh, to give medium-sized rings fused to bis-2-azetidinone, pyrrolidinyl-2-azetidinone, or piperidinyl-2-azetidinone systems. The diolefinic cyclization precursors can be obtained from optically pure 4-oxoazetidine-2-carbaldehydes bearing an extra alkene tether at position 1 or 3 of the beta-lactam ring via [2 + 2] cycloaddition of imino 2-azetidinones, N-metalated azometine ylide [3 + 2] cycloaddition, and subsequent N-acylation of the pyrrolidinyl nitrogen atom, or through aza-Diels-Alder cycloaddition of 2-azetidinone-tethered imines. Under standard reaction conditions, the combination of cycloaddition reactions of 2-azetidinone-tethered imines with ring-closing methatesis offers an asymmetric entry to a variety of unusual fused tricyclic 2-azetidinones bearing two bridgehead nitrogen atoms.
引用
收藏
页码:1426 / 1432
页数:7
相关论文
共 60 条
[1]   Metal-mediated carbonyl-1,3-butadien-2-ylation by 1,4-bis(methanesulfonyl)-2-butyne or 1,4-dibromo-2-butyne in aqueous media:: Asymmetric synthesis of 3-substituted 3-hydroxy-β-lactams [J].
Alcaide, B ;
Almendros, P ;
Rodríguez-Acebes, R .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (06) :1925-1928
[2]   Recent advances in the stereocontrolled synthesis of bi- and tricyclic-β-lactams with non-classical structure [J].
Alcaide, B ;
Almendros, P .
CURRENT ORGANIC CHEMISTRY, 2002, 6 (03) :245-264
[3]   Rapid entry to enantiopure carbacepham derivatives via Lewis acid promoted carbonyl-ene cyclization of 2-azetidinone-tethered alkenylaldehydes [J].
Alcaide, B ;
Pardo, C ;
Rodríguez-Ranera, C ;
Rodríguez-Vicente, A .
ORGANIC LETTERS, 2001, 3 (26) :4205-4208
[4]  
Alcaide B, 2002, CHEM-EUR J, V8, P3646, DOI 10.1002/1521-3765(20020816)8:16<3646::AID-CHEM3646>3.0.CO
[5]  
2-M
[6]  
Alcaide B, 2002, CHEM-EUR J, V8, P1719, DOI 10.1002/1521-3765(20020402)8:7<1719::AID-CHEM1719>3.0.CO
[7]  
2-U
[8]  
Alcaide B, 2002, SYNLETT, P381
[9]   A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM ;
Aly, MF .
ORGANIC LETTERS, 2001, 3 (23) :3781-3784
[10]   4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].
Alcaide, B ;
Almendros, P .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240