Chiral oxazolidinones from α-hydroxy oxazolidines:: a new access to 1,2-amino alcohols

被引：14
|
作者：
Agami, C [1 ]
Amiot, F [1 ]
Couty, F [1 ]
Dechoux, L [1 ]
Kaminsky, C [1 ]
Venier, O [1 ]
机构：
[1] Univ Paris 06, Lab Synth Asymetr, UMR 7611, CNRS, F-75005 Paris, France
来源：
TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 22期
关键词：
D O I：
10.1016/S0957-4166(98)00414-5
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
N-Carbamoyl-alpha-hydroxy oxazolidines prepared from N-Boc-2-acyl oxazolidines or N-Boc-2-alkenyl oxazolidines, using phenyl glycinol as the chiral source, are converted into bicyclic oxazolidinones. Reactions of these compounds with different nucleophiles under conditions suitable for the production of N-acyliminium ions were studied. Allylsilane reacted very stereoselectively in all cases, and this reaction provides a new flexible entry for the preparation of enantiopure syn-2-amino alcohols, possibly bearing an additional stereocenter ex to the hydroxyl moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3955 / 3958
页数：4
相关论文
共 50 条
  • [1] Synthesis of functionalized oxazolidines by multicomponent reactions of 1,2-amino alcohols (microreview)
    Xu, Xianjun
    Wei, Hua
    Feng, Huangdi
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (04) : 464 - 466
  • [2] A chiral ketone for enantioselective recognition of 1,2-amino alcohols
    Nandhakumar, Raju
    Guo, Yong-En
    Park, Hytinjung
    Tang, Lijun
    Nam, Wonwoo
    Kim, Kwan Mook
    TETRAHEDRON LETTERS, 2007, 48 (37) : 6582 - 6585
  • [3] Chemistry for chiral skeletons: Building chiral fragments from enantiopure 1,2-amino alcohols
    Serrano, Juan
    Boskovic, Zarko
    Ferrara, Steven
    Furst, Laura
    Figueroa, Samuel
    Crews, DeMarcus
    Guerrero, Adrian
    Brackeen, Christina
    Nelson, Shawn
    Dandapani, Sivaraman
    Phillips, Andrew
    Schreiber, Stuart
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [4] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
    Ager, DJ
    Prakash, I
    Schaad, DR
    CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
  • [5] New, convenient methods of synthesis and resolution of 1,2-amino alcohols
    Periasamy, M
    Sivakumar, S
    Reddy, MN
    SYNTHESIS-STUTTGART, 2003, (13): : 1965 - 1967
  • [6] Asymmetric Synthesis of Chiral 1,2-Amino Alcohols and Morpholin-2-ones from Arylglyoxals
    Powell, Wyatt C.
    Walczak, Maciej A.
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (17): : 10487 - 10500
  • [7] Synthesis of new tetrazole-containing 1,2-amino alcohols
    Pantileenko, SV
    Petrov, VV
    Ratner, FI
    Shchetinina, TV
    ZHURNAL ORGANICHESKOI KHIMII, 1999, 35 (03): : 479 - 480
  • [8] Efficient access to chiral 1,2-amino alcohols via Ir/f-amphox-catalyzed asymmetric hydrogenation of α-amino ketones
    Hu, Yang
    Wu, Weilong
    Dong, Xiu-Qin
    Zhang, Xumu
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (08): : 1499 - 1502
  • [9] Asymmetric synthesis of 1,2-amino alcohols using (S)-indoline chiral auxiliary
    Youn, SW
    Choi, JY
    Kim, YH
    CHIRALITY, 2000, 12 (5-6) : 404 - 407
  • [10] Unsaturated 1,2-amino alcohols and ethers from aziridines and organolithiums
    Hodgson, DM
    Stefane, B
    Miles, TJ
    Witherington, J
    CHEMICAL COMMUNICATIONS, 2004, (19) : 2234 - 2235
12345