Asymmetric synthesis of α-substituted β-formyl δ-lactones via a Michael addition/α-alkylation protocol

被引：0
|
作者：
Enders, D [1 ]
Vázquez, J [1 ]
机构：
[1] Inst Organ Chem, D-52074 Aachen, Germany
来源：
SYNLETT | 1999年 / 05期
关键词：
SAMP-hydrazone; formyl anion equivalent; alkylation of lactones; Michael addition; asymmetric synthesis;
D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient trans-diastereo- and enantioselective synthesis of alpha-substituted beta-formyl delta-lactones 5 (de greater than or equal to 98%, ee = 80-95%) is described, employing formaldehyde-SAMP-hydrazone (1) as a neutral formyl anion equivalent. The new procedure involves the Michael addition of 1 to 5,6-dihydro-2H-pyran- Zone (2) followed by trans-selective alpha-alkylation and subsequent oxidative cleavage of the auxiliary.
引用
收藏
页码：629 / 631
页数：3
相关论文
共 50 条
  • [31] Asymmetric synthesis of functionalized tetrahydrofluorenones via an NHC-catalyzed homoenolate Michael addition
    Shu, Tao
    Li, Sun
    Chen, Xiang-Yu
    Liu, Qiang
    von Essen, Carolina
    Rissanen, Kari
    Enders, Dieter
    CHEMICAL COMMUNICATIONS, 2018, 54 (55) : 7661 - 7664
  • [32] Effect of achiral and mixed chiral ligands on the asymmetric synthesis of γ-nitrophosphonates via Michael addition
    Rai, Vishal
    Namboothiri, Irishi N. N.
    TETRAHEDRON-ASYMMETRY, 2008, 19 (07) : 767 - 772
  • [33] Organocatalytic asymmetric domino reactions:: A cascade consisting of a Michael addition and an aldehyde α-alkylation
    Enders, Dieter
    Wang, Chuan
    Bats, Jan W.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) : 7539 - 7542
  • [34] Asymmetric Synthesis of β-Nitro Ketones via Michael Addition of Lithiated α-Amino Nitriles to Nitroalkenes
    Enders, Dieter
    Foerster, Dominik
    Raabe, Gerhard
    Bats, Jan W.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (24): : 9641 - 9646
  • [35] Asymmetric chroman synthesis via an intramolecular oxy-Michael addition by bifunctional organocatalysts
    Miyaji, Ryota
    Asano, Keisuke
    Matsubara, Seijiro
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) : 119 - 122
  • [36] Organocatalytic enantio- and diastereoselective synthesis of highly substituted δ-lactones via a Michael-cyclization cascade
    Agrawal, Santosh
    Molleti, Nagaraju
    Singh, Vinod K.
    CHEMICAL COMMUNICATIONS, 2015, 51 (48) : 9793 - 9796
  • [37] Catalytic asymmetric tandem Friedel-Crafts alkylation/Michael addition reaction for the synthesis of highly functionalized chromans
    Peng, Jiahuan
    Du, Da-Ming
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 1210 - 1216
  • [38] ASYMMETRIC MICHAEL ADDITIONS VIA SAMP-RAMP-HYDRAZONES ENANTIOSELECTIVE SYNTHESIS OF BETA-SUBSTITUTED DELTA-OXOPENTANOATES AND DELTA-LACTONES
    ENDERS, D
    RENDENBACH, BEM
    CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (07): : 1223 - 1227
  • [39] Enantioselective Michael Addition: An Experimental Introduction to Asymmetric Synthesis
    Tiano, Martin
    JOURNAL OF CHEMICAL EDUCATION, 2020, 97 (08) : 2291 - 2295
  • [40] DIRECT ASYMMETRIC-SYNTHESIS OF QUATERNARY CARBON CENTERS VIA ADDITION ELIMINATION PROCESS - NITROOLEFINATION OF ALPHA-SUBSTITUTED DELTA-LACTONES
    FUJI, K
    NODE, M
    NAGASAWA, H
    NANIWA, Y
    TAGA, T
    MACHIDA, K
    SNATZKE, G
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 7921 - 7925
12345