Practical Synthesis of Natural Amino Acid Derivatives: Hf(OTf)4-Catalyzed Mannich-Type Reaction of Ketene Silyl Acetals or Enol Silyl Ethers with N,O-Acetals as a Glycine Cation Equivalent

被引：14

作者：

Sakai, Norio ^{[1
]}

Sato, Asuka ^{[1
]}

Konakahara, Takeo ^{[1
]}

机构：

[1] Tokyo Univ Sci RIKADAI, Fac Sci & Technol, Dept Pure & Appl Chem, Chiba 2788510, Japan

来源：

SYNLETT | 2009年 / 09期

关键词：

Mannich-type reaction; N; O-acetal; amino acid; hafnium triflate; FRIEDEL-CRAFTS REACTION; ALPHA-AMINO; ASYMMETRIC-SYNTHESIS; PRIMARY AMINOMETHYLATION; BETA-LACTAMS; ENANTIOSELECTIVE ALKYLATIONS; ADDITION-REACTIONS; FACILE SYNTHESIS; ESTERS; N; N-BIS(TRIMETHYLSILYL)METHOXYMETHYLAMINE;

D O I：

10.1055/s-0029-1216743

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The authors demonstrated the Hf(OTf)(4)-catalyzed Mannich-type reaction of an enol silyl ether and a ketene silyl acetal with an NO-acetal leading to the preparation of amino acid derivatives. In particular, use of the N,O-acetal having a bis(trimethylsilyl)amino group directly produced N-unprotected aspartic acid derivatives after a standard aqueous workup.

引用

页码：1449 / 1452

页数：4

共 7 条

[1] Bronsted acid-catalyzed, enantioselective, vinylogous Mannich reaction of vinylketene silyl N,O-acetals
Giera, David S.
Sickert, Marcel
Schneider, Christoph
ORGANIC LETTERS, 2008, 10 (19) : 4259 - 4262
[2] Diarylborinic acid derivatives as a catalytic iminium ion generator in the Mannich-type reaction using secondary amines, aldehydes, and ketene silyl acetals
Tanaka, Yusuke
Hasui, Tomoaki
Suginome, Michinori
SYNLETT, 2008, (08) : 1239 - 1242
[3] Sulfated zirconia (SO4/ZrO2) as a reusable solid acid catalyst for the Mannich-type reaction between ketene silyl acetals and aldimines
Wang, Sainan
Matsumura, Shuichi
Toshima, Kazunobu
TETRAHEDRON LETTERS, 2007, 48 (37) : 6449 - 6452
[4] Novel one-pot mannich-type reaction in water:: Indium trichloride-catalyzed condensation of aldehydes, amines and silyl enol ethers for the synthesis of β-amino ketones and esters
Loh, TP
Wei, LL
TETRAHEDRON LETTERS, 1998, 39 (3-4) : 323 - 326
[5] Hf(OTf)4-doped Me3SiCI-catalyzed aminomethylation of arenes with N,O-Acetals:: Facile approach to non-natural aromatic amino acid precursors
Sakai, Norio
Asano, Junichi
Shimano, Yuta
Konakahara, Takeo
SYNLETT, 2007, (17) : 2675 - 2678
[6] One-Pot Synthesis of.-Halo.-Amino Acid Derivatives via the Difunctional Coupling of Ethyl.-Diazoacetate with Silyl Halides and N,O-Acetals or Aromatic Tertiary Amines
Sakai, Norio
Sasaki, Kazuki
Suzuki, Hiroki
Ogiwara, Yohei
SYNTHESIS-STUTTGART, 2020, 52 (12): : 1823 - 1832
[7] Zr(OTf)4-catalyzed direct three-component Mannich-type reaction of carbamates:: An efficient one-step synthesis of N-protected β-aryl-β-amino ketones
Yang, Lei
Xu, Li-Wen
Sun, Wei
Xia, Chun-Gu
LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (01) : 34 - 37

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