Construction of C-S bonds with a quaternary stereocenter through a formal Michael reaction:: Asymmetric synthesis of tertiary thiols

被引：34

作者：

Palomo, C

Oiarbide, M

Dias, F

López, R

Linden, A

机构：

[1] Univ Basque Country, Fac Quim, Dept Quim Organ 1, E-20080 San Sebastian, Spain

[2] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 25期

关键词：

asymmetric synthesis; chirality; Lewis acids; Michael addition; thiols;

D O I：

10.1002/anie.200453889

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quaternary stereocenters that bear a sulfur substituent can be created with nearly perfect stereocontrol through an intramolecular Michael-type process. Lewis acids (L.A.) accelerate the intramolecular sulfur-atom transfer from the oxazolidine-2-thione functionality to the β carbon atom of the β,β-disubstituted enoyl moiety, whereas the chirality of the oxazolidine-2-thione portion controls reaction stereochemistry (see scheme).

引用

页码：3307 / 3310

页数：4

共 46 条

[1] CONSTRUCTION OF CONTIGUOUS QUATERNARY AND TERTIARY CARBON CENTERS VIA THE ASYMMETRIC MICHAEL REACTION
TOMIOKA, K
YASUDA, K
KOGA, K
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (18) : 1345 - 1346
[2] Construction of Asymmetric C-S Bonds via an Electrochemical Catalysis
Sun, Xiang
Zhang, Yan
Li, Tong
Li, Kai
Sun, Qi
Wang, Zhiyong
ORGANIC LETTERS, 2024, 26 (08) : 1566 - 1572
[3] Vicinal All-Carbon Quaternary Stereocenter Construction with Trifluoromethyl Groups via Organocatalytic Asymmetric Cascade Michael/Michael Reaction
Tsuyusaki, Ryo
Nakashima, Kosuke
Matsushima, Yasuyuki
Hirashima, Shin-ichi
Miura, Tsuyoshi
CHEMISTRY-AN ASIAN JOURNAL, 2024, 19 (01)
[4] Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes Bearing a Quaternary Stereocenter via Double Michael Reaction Involving Dynamic Kinetic Resolution
Meninno, Sara
Croce, Gianluca
Lattanzi, Alessandra
ORGANIC LETTERS, 2013, 15 (13) : 3436 - 3439
[5] Asymmetric Construction of Vicinal Stereocenters Containing Quaternary and Tertiary Carbons: Application to the Formal Synthesis of (-)-Chenopodene
Harada, Kenichi
Ibaragi, Daisuke
Edazawa, Yui
Sakashita, Masanori
Nakata, Ayane
Kubo, Miwa
Carter, Rich G.
Fukuyama, Yoshiyasu
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (04) : 420 - 423
[6] Al-Catalyzed Facile Construction of Quaternary C-C Bonds by the Allylic Substitution of Tertiary Alcohols: A Concise and Formal Synthesis of (±)-Mersicarpine
Zhong, Xue
Li, You
Han, Fu-She
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (32) : 9784 - 9788
[7] Construction of Quaternary Carbon Stereocenter of α-Tertiary Amine through Remote C-H Functionalization of Tris Derivatives: Enantioselective Total Synthesis of Myriocin
Miyagawa, Takashi
Inuki, Shinsuke
Oishi, Shinya
Ohno, Hiroaki
ORGANIC LETTERS, 2019, 21 (14) : 5485 - 5490
[8] Organocatalytic Asymmetric Synthesis of Pentasubstituted Tetrahydrothiopyrans Bearing a Quaternary Centre through a Double Michael Reaction
Mondal, Buddhadeb
Pan, Subhas Chandra
SYNLETT, 2018, 29 (05) : 576 - 580
[9] The solvent-controlled chemoselective construction of C-S/S-S bonds via the Michael reaction/thiol coupling of quinoline-2-thiones
Zhang, Xi
Wang, Tong-Lin
Liu, Xiao-Jun
Wang, Xi-Cun
Quan, Zheng-Jun
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (09) : 2379 - 2383
[10] One-Pot Synthesis of Benzoxazole/Benzothiazole-Substituted Esters by Michael Addition: A Selective Construction of C-N/C-S Bonds
Gong, Zhi-Ying
Yang, Cheng-Li
Wang, Dan
Huang, Lang
Dong, Zhi-Bing
CATALYSTS, 2023, 13 (04)

← 1 2 3 4 5 →