N1-C4 β-lactam bond cleavage in the 2-(trimethylsilyl)thiazole addition to β-lactam aldehydes:: Asymmetric synthesis of spiranic and tertiary α-alkoxy-γ-keto acid derivatives

被引：13

作者：

Alcaide, Benito ^{[1
]}

Almendros, Pedro

Redondo, Maria C.

机构：

[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain

[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 22期

关键词：

aldehydes; asymmetric synthesis; cleavage reactions; lactams; spiro compounds;

D O I：

10.1002/ejoc.200700231

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Starting substrates, enantiopure spiranic or 3-substituted 3-alkoxy-4-oxoazetidine-2-carbaldehydes, were prepared from (R)-2,3-O-isopropylideneglyceraldehyde derived azetidine-2,3-diones by sequential Barbier-type addition reactions followed by hydroxy functionalization and aldehyde unmasking. The reaction between the above beta-lactam aldehydes and 2-(trimethylsilyl)thiazole (TMST) gave as major products conformationally constrained alpha-alkoxy-gamma-keto amides, which can be considered both as aldols as well as Passerini-type products, by N1-C4 beta-lactam bond cleavage. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：3707 / 3710

页数：4

共 42 条

[1] Efficient entry to diversely functionalized spirocyclic oxindoles from isatins through carbonyl-addition/cyclization reaction sequences [J].

Alcaide, B ;

Almendros, P ;

Rodríguez-Acebes, R .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (06) :2346-2351

[2] A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (10) :2874-2879

[3] Synthesis of strained tricyclic β-lactams by intramolecular [2+2] cycloaddition reactions of 2-azetidinone-tethered enallenols:: Control of regioselectivity by selective alkene substitution [J].

Alcaide, B ;

Almendros, P ;

Aragoncillo, C ;

Redondo, MC ;

Torres, MR .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (05) :1539-1546

[4] Organocatalytic ring expansion of β-lactams to γ-lactams through a novel N1-C4 bond cleavage.: Direct svnthesis of enantiopure succinimide derivatives [J].

Alcaide, B ;

Almendros, P ;

Cabrero, G ;

Ruiz, MP .

ORGANIC LETTERS, 2005, 7 (18) :3981-3984

[5] Novel N1-C4 β-lactam bond breakage.: Synthesis of enantiopure α-alkoxy-γ-keto acid derivatives [J].

Alcaide, B ;

Almendros, P ;

Redondo, MC .

ORGANIC LETTERS, 2004, 6 (11) :1765-1767

[6] β-lactams as versatile synthetic intermediates for the preparation of heterocycles of biological interest [J].

Alcaide, B ;

Almendros, P .

CURRENT MEDICINAL CHEMISTRY, 2004, 11 (14) :1921-1949

[7] Synthesis of optically pure highly functionalized γ-lactams via 2-azetidinone-tethered iminophosphoranes [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :993-996

[8]

Alcaide B, 2002, CHEM-EUR J, V8, P1719, DOI 10.1002/1521-3765(20020402)8:7<1719::AID-CHEM1719>3.0.CO

[9]

2-U

[10]

Alcaide B, 2002, SYNLETT, P381

← 1 2 3 4 5 →