2,6-Disubstituted and 2,2,6-Trisubstituted Piperidines from Serine: Asymmetric Synthesis and Further Elaboration

被引:14
|
作者
Acharya, Hukum P. [1 ]
Clive, Derrick L. J. [1 ]
机构
[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada
来源
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 15期
基金
加拿大自然科学与工程研究理事会;
关键词
RING-CLOSING METATHESIS; CLAISEN REARRANGEMENT; DIASTEREOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; QUINOLIZIDINE ALKALOIDS; EFFICIENT; INDOLIZIDINE; PYRROLIDINE; CYCLIZATION; ACETALS;
D O I
10.1021/jo101010c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Hydroxy-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl esters, which are readily prepared from serine and terminal acetylenes, undergo Claisen rearrangement to piperidine derivatives when heated with butyl vinyl ether in the presence of Hg(OAc)(2) and Et(3)N. This route to optically pure piperidines having substituents alpha to nitrogen is general, and the rearrangement products are versatile intermediates for making a broad range of amines containing a substituted piperidine subunit.
引用
收藏
页码:5223 / 5233
页数:11
相关论文
共 50 条
  • [31] Asymmetric Synthesis of 2,3,4-Trisubstituted Piperidines
    Kriis, Kadri
    Melnik, Triin
    Lips, Kristiina
    Juhanson, Ilona
    Kaabel, Sandra
    Jarving, Ivar
    Kanger, Tonis
    SYNTHESIS-STUTTGART, 2017, 49 (03): : 604 - 614
  • [32] DIRECT SYNTHESIS OF 2,6-DISUBSTITUTED PYRIDINES FROM BICYCLIC KETALS
    JUN, JG
    SHIN, HS
    KIM, SH
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (15): : 1815 - 1818
  • [33] Synthesis of 2,4,6-trisubstituted chiral piperidines and (-)-dendroprimine by one-pot asymmetric azaelectrocyclization protocol
    Kobayashi, Toyoharu
    Hasegawa, Futoshi
    Tanaka, Katsunori
    Katsumura, Shigeo
    ORGANIC LETTERS, 2006, 8 (17) : 3813 - 3816
  • [34] A NOVEL ASYMMETRIC ROUTE TO CHIRAL, NON-RACEMIC 2-SUBSTITUTED AND CIS-2,6-DISUBSTITUTED PIPERIDINES
    MUNCHHOF, MJ
    MEYERS, AI
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 287 - ORGN
  • [35] Structures of 2,6-disubstituted naphthalenes
    Kaduk, J.A.
    Golab, J.T.
    Acta Crystallographica, Section B: Structural Science, 1999, 55 (pt 1):
  • [36] NOVEL 2,6-DISUBSTITUTED AZULENES
    BALSCHUKAT, D
    DEHMLOW, EV
    CHEMISCHE BERICHTE-RECUEIL, 1986, 119 (07): : 2272 - 2288
  • [37] REARRANGEMENTS OF 2,6-DISUBSTITUTED ARYLHYDRAZIDES
    FUSCO, R
    SANNIKOLO, F
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1978, (04): : 504 - 507
  • [38] MESOMORPHISM OF 2,6-DISUBSTITUTED NAPHTHALENES
    KARAMYSHEVA, LA
    KOVSHEV, EI
    TITOV, VV
    ZHURNAL ORGANICHESKOI KHIMII, 1976, 12 (12): : 2628 - 2629
  • [39] Structures of 2,6-disubstituted naphthalenes
    Kaduk, JA
    Golab, JT
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1999, 55 : 85 - 94
  • [40] Solid-phase synthesis of 4,6-disubstituted and 3,4,6-trisubstituted pyrid-2-ones
    Katritzky, AR
    Chassaing, C
    Barrow, SJ
    Zhang, ZH
    Vvedensky, V
    Forood, B
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (04): : 249 - 250