ASYMMETRIC DIELS-ALDER REACTION OF OPTICALLY-ACTIVE ALPHA-(2-EXO-HYDROXY-10-BORNYL)SULFINYLMALEIMIDES AND ITS APPLICATION TO OPTICALLY-ACTIVE 5-FUNCTIONALIZED PYRROLINES VIA RETRO-DIELS-ALDER REACTION

被引:34
作者
ARAI, Y
MATSUI, M
FUJII, A
KONTANI, T
OHNO, T
KOIZUMI, T
SHIRO, M
机构
[1] TOYAMA MED & PHARMACEUT UNIV,FAC PHARMACEUT SCI,TOYAMA 93001,JAPAN
[2] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 01期
关键词
D O I
10.1039/p19940000025
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Optically pure sulfinylmaleimides 1 have been synthesized. The Diels-Alder reactions of the sulfoxides 1 with various dienes showed high diasteroselectivity. Regioselective reduction of the adducts 4c and 6c followed by desulfinylation afforded the gamma-hydroxy lactams 17 and 27, respectively. N-Acyliminium additions using compounds 17 and 27 proceeded diastereoselectively to give gamma-alkyl lactams 23 and 29 by virtue of its conformationally rigid, bicyclo[2.2.1]- and 7-oxabicyclo[2.2.1]-heptene moiety. respectively. The use of compound 29 allows a simple preparation of chirally 5-functionalised Delta(3)-pyrrolin-2-ones of high optical purity such as compound 25 via retro-Diels-Alder reaction, whereas the thermal cycloreversion of adduct 23 required such forcing conditions as flash vacuum pyrolysis.
引用
收藏
页码:25 / 39
页数:15
相关论文
共 64 条
  • [1] ARAI Y, 1990, SYNTHESIS-STUTTGART, P320
  • [2] ARAI Y, 1992, CHEM PHARM BULL, V40, P1670
  • [3] SYNTHESIS AND ASYMMETRIC DIELS-ALDER REACTION OF DIMETHYL (D-ISOBORNEOL-10-SULPHINYL)MALEATE - NOVEL ROUTE TO KEY INTERMEDIATES FOR SYNTHESIS OF SOME CARBOCYCLIC NUCLEOSIDES AND TERPENOIDS
    ARAI, Y
    HAYASHI, K
    MATSUI, M
    KOIZUMI, T
    SHIRO, M
    KURIYAMA, K
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07): : 1709 - 1716
  • [4] POWERFUL DIENOPHILES FOR ASYMMETRIC DIELS-ALDER REACTIONS - ALPHA-(2-EXO-HYDROXY-10-BORNYLSULFINYL)MALEIMIDES
    ARAI, Y
    MATSUI, M
    KOIZUMI, T
    SHIRO, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 1983 - 1985
  • [5] ARAI Y, 1992, REV HETEROATOM CHEM, V6, P202
  • [6] SYNTHESIS AND PROPERTIES OF PYRROLIN-2-ONES
    BAKER, JT
    SIFNIADES, S
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (15) : 2798 - 2800
  • [7] (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL FOR ASYMMETRIC-SYNTHESIS
    BALDWIN, JE
    MOLONEY, MG
    SHIM, SB
    [J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1379 - 1380
  • [8] DIASTEREOSELECTIVE DIELS-ALDER REACTIONS BETWEEN SUBSTITUTED 1,3-BUTADIENES AND N-ALPHA-METHYLBENZYLMALEIMIDE
    BALDWIN, SW
    GREENSPAN, P
    ALAIMO, C
    MCPHAIL, AT
    [J]. TETRAHEDRON LETTERS, 1991, 32 (42) : 5877 - 5880
  • [9] BRAISH TF, 1992, SYN LETT, V12, P979
  • [10] BROWN DS, 1990, SYNLETT, V12, P749