Ru(II)- and Ir(I) Catalyzed Hydrogen Peroxide Oxidation of Hydroxamic Acids and their Subsequent Hetero Diels-Alder Cycloadditions with Chiral N-Dienyl Lactams

被引：4
作者：
Fakhruddin, Ahmad [1 ]
Phomkeona, Kesiny [1 ]
Abu-Elfotoh, Abdel-Moneim [1 ]
Shibatomi, Kazutaka [1 ]
Iwasa, Seiji [1 ]
机构：
[1] Toyohashi Univ Technol, Sch Mat Sci, Aichi 4418580, Japan
来源：
LETTERS IN ORGANIC CHEMISTRY | 2010年 / 7卷 / 06期
关键词：
Nitroso intermediate; hydrogen peroxide; ruthenium catalyst; iridium catalyst; hetero Diels-Alder reaction; 1; 2-oxazine; ASYMMETRIC-SYNTHESIS; ACYL;
D O I：
10.2174/157017810791824955
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric hetero Diels-Alder (HDA) reaction of highly reactive acyl nitroso intermediates are reported. Transient acyl nitroso compounds 2a'-c' are formed by Ru(II)- or Ir(I)-catalyzed hydrogen peroxide oxidation of hydroxamic acids 2a-c and are trapped in situ by the optically pure N-dienyl-L-pyroglutamates 1a-b to afford the corresponding diastereomeric adducts 3a-f and 4a-f up to 98% yield (70% de) and 72% de (70% yield) with complete regioselectivity at 0 degrees C to room temperature.
引用
收藏
页码：475 / 478
页数：4
相关论文
共 15 条
  • [1] Chiral N-dienyl-L-pyroglutamic esters in asymmetric hetero-Diels-Alder reactions with acylnitroso dienophiles
    Behr, JB
    Defoin, A
    Pires, J
    Streith, J
    Macko, L
    Zehnder, M
    [J]. TETRAHEDRON, 1996, 52 (09) : 3283 - 3302
  • [2] Direct observation of an acyl nitroso species in solution by time-resolved IR spectrocopy
    Cohen, AD
    Zeng, BB
    King, SB
    Toscano, JP
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) : 1444 - 1445
  • [3] The first enantioselective hetero Diels-Alder reaction of nitroso compound utilizing tartaric acid ester as a chiral auxiliary
    Ding, X
    Ukaji, Y
    Fujinami, S
    Inomata, K
    [J]. CHEMISTRY LETTERS, 2003, 32 (07) : 582 - 583
  • [4] A rapid and efficient synthesis of quinone derivatives: Ru(II)- or Ir(I)-catalyzed hydrogen peroxide oxidation of phenols and methoxyarenes
    Iwasa, S
    Fakhruddin, A
    Widagdo, HS
    Nishiyama, H
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) : 517 - 520
  • [5] Synthesis of acylnitroso intermediates and their synthetic applications
    Iwasa, S
    Fakhruddin, A
    Nishiyama, H
    [J]. MINI-REVIEWS IN ORGANIC CHEMISTRY, 2005, 2 (02) : 157 - 175
  • [6] Iridium(I)-catalyzed hydrogen peroxide oxidation of hydroxamic acids and hetero Diels-Alder reaction of the acyl nitroso intermediates with cyclopentadiene
    Iwasa, S
    Fakhruddin, A
    Tsukamoto, Y
    Kameyama, M
    Nishiyama, H
    [J]. TETRAHEDRON LETTERS, 2002, 43 (35) : 6159 - 6161
  • [7] A mild oxidation method of hydroxamic acids: efficient trapping of acyl nitroso intermediates
    Iwasa, S
    Tajima, K
    Tsushima, S
    Nishiyama, H
    [J]. TETRAHEDRON LETTERS, 2001, 42 (34) : 5897 - 5899
  • [8] Racemic and asymmetric Diels-Alder reactions of 1-(2-oxazolidinon-3-yl)-3-siloxy-1,3-butadienes
    Janey, JM
    Iwama, T
    Kozmin, SA
    Rawal, VH
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) : 9059 - 9068
  • [9] Chiral amino siloxy dienes in the Diels-Alder reaction:: Applications to the asymmetric synthesis of 4-substituted and 4,5-disubstituted cyclohexenones and the total synthesis of (-)-α-elemene
    Kozmin, SA
    Rawal, VH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) : 9562 - 9573
  • [10] ETHYL N-DIENYL PYROGLUTAMATES - NOVEL ASYMMETRIC DIENES
    MENEZES, RF
    ZEZZA, CA
    SHEU, J
    SMITH, MB
    [J]. TETRAHEDRON LETTERS, 1989, 30 (25) : 3295 - 3298
12