ASYMMETRIC-SYNTHESIS OF SYN 1,2-DIOLS VIA THE REACTION OF ALDEHYDES WITH CHIRAL GAMMA-(TETRAHYDROPYRANYLOXY)ALLYLSTANNANES

被引:28
|
作者
YAMAMOTO, Y
KOBAYASHI, K
OKANO, H
KADOTA, I
机构
[1] Department of Chemistry, Faculty of Science, Tohoku University
来源
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 26期
关键词
D O I
10.1021/jo00052a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric synthesis of syn 1,2-diols 3 has been accomplished via the reaction of the chiral gamma-alkoxy-substituted allylstannane 1 with aldehydes in the presence of AlCl3 or AlCl3.OEt2, followed by a five-step operation to remove the chiral auxiliary.
引用
收藏
页码:7003 / 7005
页数:3
相关论文
共 50 条
  • [21] CHIRAL HOMOENOLATE EQUIVALENTS .1. ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED ALDEHYDES VIA METALATED CHIRAL ALLYLAMINES
    AHLBRECHT, H
    BONNET, G
    ENDERS, D
    ZIMMERMANN, G
    TETRAHEDRON LETTERS, 1980, 21 (33) : 3175 - 3178
  • [22] Epoxide hydrolase-catalyzed enantioselective synthesis of chiral 1,2-diols via desymmetrization of meso-epoxides
    Zhao, LS
    Han, B
    Huang, ZL
    Miller, M
    Huang, HJ
    Malashock, DS
    Zhu, ZL
    Milan, A
    Robertson, DE
    Weiner, DP
    Burk, MJ
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (36) : 11156 - 11157
  • [23] Synthesis and use of chiral substituted benzenes containing 1,2-diols protected as cyclic acetals
    Ramarao, Chandrashekar
    Nandipati, Ramadevi
    Navakoti, Rajasekhar
    Kottamasu, Ramanjaneyulu
    TETRAHEDRON LETTERS, 2012, 53 (06) : 637 - 640
  • [24] A Chiral Benzyl Group as a Chiral Auxiliary and Protecting Group for the Synthesis of Optically Active 1,2-Diols and (+)-Frontalin
    Kim, Tae Hyun
    Kim, Young-Kyo
    Yang, Zunhua
    Jung, Jung Wha
    Jeong, Lak Shin
    Kim, Hee-Doo
    SYNLETT, 2014, 25 (02) : 251 - 254
  • [25] Facile synthesis of enantiopure 1,2-diols and terminal Epoxides from chiral β-hydroxy sulfides
    Cho, BT
    Choi, OK
    Kim, DJ
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2003, 24 (07) : 1023 - 1025
  • [26] Effect of ionic liquids on epoxide hydrolase-catalyzed synthesis of chiral 1,2-diols
    Chiappe, Cinzia
    Leandri, Elsa
    Hammock, Bruce D.
    Morisseau, Christophe
    GREEN CHEMISTRY, 2007, 9 (02) : 162 - 168
  • [27] Ruthenium- and lipase-catalyzed DYKAT of 1,2-diols:: an enantioselective synthesis of syn-1,2-diacetates
    Edin, M
    Martín-Matute, B
    Bäckvall, JE
    TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 708 - 715
  • [28] Amino Acid Salt Catalyzed Asymmetric Synthesis of 1,2-Diols with A Quaternary Carbon Center
    Wu, Quanquan
    Liu, Shulei
    Wang, Fangyuan
    Li, Qingqing
    Cheng, Kangli
    Li, Juan
    Jiang, Jun
    SYNLETT, 2015, 26 (17) : 2442 - 2446
  • [29] Asymmetric synthesis of new chiral 1,2- and 1,3-diols
    Tülay Yıldız
    Ayşe Yusufoğlu
    Monatshefte für Chemie - Chemical Monthly, 2013, 144 : 183 - 190
  • [30] Asymmetric synthesis of new chiral 1,2-and 1,3-diols
    Yildiz, Tulay
    Yusufoglu, Ayse
    MONATSHEFTE FUR CHEMIE, 2013, 144 (02): : 183 - 190