Asymmetric synthesis of 1-substituted 2-azaspiro[3.3]heptanes: important motifs for modern drug discovery

被引:11
|
作者
Reddy, Leleti Rajender [1 ]
Waman, Yogesh [1 ]
Kallure, Priya [1 ]
Nalivela, Kumara Swamy [1 ]
Begum, Zubeda [1 ]
Divya, Thumbar [1 ]
Kotturi, Sharadsrikar [1 ]
机构
[1] Piramal Discovery Solut, Route Scouting Dept, Sarkhej Bavla Highway, Ahmadabad 382213, Gujarat, India
关键词
TERT-BUTANESULFINYL IMINES; AMINO-ACIDS; SULFINIMINES; ANTI-2,3-DIAMINO; OPTIMIZATION; PROTOCOL;
D O I
10.1039/c9cc00863b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly diastereoselective addition of ethyl cyclobutanecarboxylate anions to Davis-Ellman's imines is reported. Thismethodology afforded the preparation of enantiomerically and diastereomerically pure 1-substituted 2-azaspiro[3.3] heptanes. This three-step procedure proceeded efficiently (yield up to 90%) and diastereoselectively (dr values up to 98 : 2). This methodology is applicable to the synthesis of 1-substituted 2-azaspiro[3.4] octane and 1-substituted 2-azaspiro[3.5]nonane.
引用
收藏
页码:5068 / 5070
页数:3
相关论文
共 31 条
  • [21] Synthesis and Rearrangement of 1-Substituted 3,3,7-Trimethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
    Yu. V. Nifontov
    V. A. Glushkov
    O. G. Ausheva
    Yu. V. Shklyaev
    Russian Journal of Organic Chemistry, 2002, 38 : 1386 - 1387
  • [22] Synthesis and rearrangement of 1-substituted 3,3,7-trimethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones
    Nifontov, YV
    Glushkov, VA
    Ausheva, OG
    Shklyaev, YV
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (09) : 1386 - 1387
  • [23] Synthesis of 1,2,4-substituted imidazoles for a fragment-based drug discovery library
    Lafferty, Tyler
    Patrone, James
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [24] A new entry to asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing a pyroglutamic acid derivative as a chiral auxiliary
    Itoh, T
    Nagata, K
    Yokoya, M
    Miyazaki, M
    Ikeda, S
    Matsuya, Y
    Enomoto, Y
    Ohsawa, A
    SYNLETT, 2002, (06) : 1005 - 1007
  • [25] ASYMMETRIC-SYNTHESIS OF 1-SUBSTITUTED TETRAHYDROISOQUINOLINES BY NUCLEOPHILIC-ADDITION TO HYDRAZONIUM IONS - APPLICATION TO THE ENANTIOSELECTIVE SYNTHESES OF (+)-SALSOLIDINE AND (-)-SALSOLIDINE AND (-)-CRYPTOSTYLINE-2
    SUZUKI, H
    AOYAGI, S
    KIBAYASHI, C
    TETRAHEDRON LETTERS, 1995, 36 (37) : 6709 - 6712
  • [26] A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries
    Itoh, T
    Miyazaki, M
    Ikeda, S
    Nagata, K
    Yokoya, M
    Matsuya, Y
    Enomoto, Y
    Ohsawa, A
    TETRAHEDRON, 2003, 59 (19) : 3527 - 3536
  • [27] Stereospecific reduction with retention of chiral fluoral-derived 1,3-oxazolidines with LiAlH4:: Asymmetric synthesis of 1-substituted 2,2,2-trifluoroethylamines
    Ishii, A
    Miyamoto, F
    Higashiyama, K
    Mikami, K
    CHEMISTRY LETTERS, 1998, (02) : 119 - 120
  • [28] Synthesis of 1-substituted (R,S)-8-(2-methoxy-5-methylphenyl)-3,3,9-trimethyl-2-azaspiro[4.5]deca-1,7-dien-6-ones
    Yu. V. Shklyaev
    Yu. V. Nifontov
    A. S. Shashkov
    S. I. Firgang
    Russian Chemical Bulletin, 2002, 51 : 2234 - 2237
  • [29] Synthesis of 1-substituted (R,S)-8-(2-methoxy-5-methylphenyl)-3,3,9-trimethyl-2-azaspiro[4.5]deca-1,7-dien-6-ones
    Shklyaev, YV
    Nifontov, YV
    Shashkov, AS
    Firgang, SI
    RUSSIAN CHEMICAL BULLETIN, 2002, 51 (12) : 2234 - 2237
  • [30] Ritter reaction. Synthesis of 1-substituted 3,3,7,9-tetramethyl-2-azaspiro[4.5]deca-6,9-dien- and -1,6,9-trien-8-ones and 7-methoxy-3,3,6,8-tetramethyl-3,4-dihydroisoquinolines
    Yu. S. Rozhkova
    K. A. Galata
    T. S. Vshivkova
    Yu. V. Shklyaev
    Russian Journal of Organic Chemistry, 2013, 49 : 1055 - 1061