A Simple, Scalable Synthetic Route to (+)- and (-)-Pseudoephenamine

被引：18
|
作者：
Mellem, Kevin T. [1 ]
Myers, Andrew G. [1 ]
机构：
[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 21期
基金：
美国国家科学基金会;
关键词：
IMINO-GROUP REDUCTION; ASYMMETRIC TRANSFER HYDROGENATION; 3 CHIRAL CENTERS; STEREOSELECTIVE-SYNTHESIS; AMINO-ALCOHOLS; STEREOCHEMISTRY; PSEUDOEPHENAMINE; BENZILS; SALTS;
D O I：
10.1021/ol402815d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A three-step synthesis of pseudoephenamine suitable for preparing multigram amounts of both enantiomers of the auxiliary from the inexpensive starting material benzil is described. The sequence involves synthesis of the crystalline monomethylimine derivative of benzil, reduction of that substance with lithium aluminum hydride, and resolution of pseudoephenamine with mandelic acid.
引用
收藏
页码：5594 / 5597
页数：4
相关论文
共 50 条
  • [1] SIMPLE SYNTHETIC ROUTE TO LASIODIPLODIN
    DANISHEFSKY, S
    ETHEREDGE, SJ
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (25): : 4716 - 4717
  • [2] Simple and Scalable Synthetic Route for Tunable Compositions of Multimetallic Oxyfluorides as Oxygen Evolution Reaction Catalysts
    Terry, Alexandre
    Mathiot, Samuel
    Guiet, Amandine
    Boivin, Edouard
    Gohari-bajestani, Zahra
    Maisonneuve, Vincent
    Hemon-Ribaud, Annie
    Moury, Romain
    Kornienko, Nikolay
    Lhoste, Jerome
    ACS APPLIED ENERGY MATERIALS, 2024, 7 (24): : 11466 - 11474
  • [3] Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin
    Fricke, Janis
    Kargbo, Robert
    Regestein, Lars
    Lenz, Claudius
    Peschel, Gundela
    Rosenbaum, Miriam A.
    Sherwood, Alexander
    Hoffmeister, Dirk
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (37) : 8281 - 8285
  • [4] A SIMPLE SYNTHETIC ROUTE TO SUBSTITUTED CYCLOPENTENOLONES
    BROWN, RT
    BLACKSTOCK, WP
    WINGFIELD, M
    TETRAHEDRON LETTERS, 1984, 25 (17) : 1831 - 1834
  • [5] SIMPLE SYNTHETIC ROUTE TO THE LIMONOID SYSTEM
    COREY, EJ
    REID, JG
    MYERS, AG
    HAHL, RW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) : 918 - 919
  • [6] A SIMPLE SYNTHETIC ROUTE TO N-SULFONYLAMIDINES
    BURGER, K
    HOSS, E
    CHEMIKER-ZEITUNG, 1988, 112 (11): : 349 - 350
  • [7] A simple and convenient synthetic route to Ulipristal acetate
    Yu, Yongguo
    He, Yun
    Zhao, Yi
    Hai, Li
    Wu, Yong
    STEROIDS, 2013, 78 (12-13) : 1293 - 1297
  • [8] A SIMPLE SYNTHETIC ROUTE TO DL-SIRENIN
    COREY, EJ
    ACHIWA, K
    TETRAHEDRON LETTERS, 1970, (26) : 2245 - &
  • [9] Simple synthetic route to polyhydroxylated pyrrolidines and piperidines
    Lee, SG
    Park, KH
    Yoon, YJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (03) : 711 - 715
  • [10] A SIMPLE SYNTHETIC ROUTE TO STATINE AND STATINE ANALOGS
    REETZ, MT
    DREWES, MW
    MATTHEWS, BR
    LENNICK, K
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (19) : 1474 - 1475
12345