Conjugate addition to (α,β)(α′,β′)-diendioate esters by lithium (α-methylbenzyl)benzylamide:: tandem addition-cyclisation versus double addition

被引：28

作者：

Urones, JG

Garrido, NM

Díez, D

Dominguez, SH

Davies, SG

机构：

[1] Univ Salamanca, Dept Quim Organ, Salamanca 37008, Spain

[2] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

TETRAHEDRON-ASYMMETRY | 1999年 / 10卷 / 09期

关键词：

D O I：

10.1016/S0957-4166(99)00170-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Strategies for obtaining either the products from tandem conjugate addition-cyclisation or from double addition in the highly stereoselective addition of lithium (R)-(alpha-methylbenzyl)benzylamide to (alpha,beta)(alpha',beta')-diendioate esters are demonstrated. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1637 / 1641

页数：5

相关论文

共 24 条

[11] Diastereo- and enantioselective synthesis of C-2-symmetric, protected 1,n-diamines from dialdehydes [J].

Enders, D ;

Meiers, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (19) :2261-2263

[12]

Gawley R.E., 1996, PRINCIPLES ASYMMETRI

[13]

IKEDA M, 1972, TETRAHEDRON LETT, P4977

[14] SYNTHESIS OF 8-MEMBERED CYCLIC SULFAMIDES - NOVEL HIV-1 PROTEASE INHIBITORS [J].

JADHAV, PK ;

WOERNER, FJ .

TETRAHEDRON LETTERS, 1995, 36 (36) :6383-6386

[15] ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS .2. PREPARATION OF THE LIKE STEREOISOMERS OF 2-METHYL-3-AMINOBUTANOIC ACID AND 2-BENZYL-3-AMINOBUTANOIC ACID [J].

JUARISTI, E ;

ESCALANTE, J ;

LAMATSCH, B ;

SEEBACH, D .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2396-2398

[16] VANADIUM(II)-INDUCED AND NIOBIUM(III)-INDUCED, DIASTEREOSELECTIVE PINACOL COUPLING OF PEPTIDE ALDEHYDES TO C-2-SYMMETRICAL HIV-PROTEASE INHIBITORS [J].

KAMMERMEIER, B ;

BECK, G ;

JACOBI, D ;

JENDRALLA, H .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (06) :685-687

[17] RATIONAL DESIGN OF POTENT, BIOAVAILABLE, NONPEPTIDE CYCLIC UREAS AS HIV PROTEASE INHIBITORS [J].

LAM, PYS ;

JADHAV, PK ;

EYERMANN, CJ ;

HODGE, CN ;

RU, Y ;

BACHELER, LT ;

MEEK, JL ;

OTTO, MJ ;

RAYNER, MM ;

WONG, YN ;

CHANG, CH ;

WEBER, PC ;

JACKSON, DA ;

SHARPE, TR ;

ERICKSONVIITANEN, S .

SCIENCE, 1994, 263 (5145) :380-384

[18] ETA-1-(1S, 2E)-1-(N,N-DIISOPROPYLCARBAMOYLOXY)-3-TRIMETHYLSILYLALLYLLITHIUM.(-)-SPARTEINE - STRUCTURE OF A CHIRAL, CARBAMOYLOXY-SUBSTITUTED ALLYLLITHIUM COMPOUND [J].

MARSCH, M ;

HARMS, K ;

ZSCHAGE, O ;

HOPPE, D ;

BOCHE, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (03) :321-323

[19] Stereoselective synthesis of HIV-1 protease inhibitor, DMP 323 [J].

Pierce, ME ;

Harris, GD ;

Islam, Q ;

Radesca, LA ;

Storace, L ;

Waltermire, RE ;

Wat, E ;

Jadhav, PK ;

Emmett, GC .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :444-450

[20] Syn-selective Michael addition of amines to bis-enones: Synthesis of 1,3,4,7-tetrasubstituted (4R,5S,6S,7R)-hexahydro-5,6-dihydroxy-2H-1,3-diazepin-2-ones [J].

Schreiner, EP ;

Pruckner, A .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5380-5384