Synthesis of N-acyl-N,O-acetals from N-aryl amides and acetals in the presence of TMSOTf

被引：21

作者：

Downey, C. Wade ^{[1
]}

Fleisher, Alan S. ^{[1
]}

Rague, James T. ^{[1
]}

Safran, Chelsea L. ^{[1
]}

Venable, Megan E. ^{[1
]}

Pike, Robert D. ^{[2
]}

机构：

[1] Univ Richmond, Dept Chem, Richmond, VA 23173 USA

[2] Coll William & Mary, Dept Chem, Williamsburg, VA 23187 USA

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 37期

关键词：

N; O-Acetal; Silyl triflate; Silyl trifluoromethanesulfonate; Silyl imidate; INTERMOLECULAR ADDITION-REACTIONS; IRCINIASTATIN; ACID;

D O I：

10.1016/j.tetlet.2011.07.023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Secondary amides undergo in situ silyl imidate formation mediated by TMSOTf and an amine base, followed by addition to acetal acceptors to provide N-acyl-N,O-acetals in good yields. An analogous, high-yielding reaction is observed with 2-mercaptothiazoline as the silyl imidate precursor. Competing reduction of the acetal to the corresponding methyl ether via transfer hydrogenation can be circumvented by the replacement of CY2NMe with 2,6-lutidine under otherwise identical reaction conditions. (C) 2011 Elsevier Ltd. All rights reserved.

引用

收藏

页码：4756 / 4759

页数：4

相关论文

共 29 条

[1] Psymberin, a potent sponge-derived cytotoxin from Psammocinia distantly related to the pederin family [J].

Cichewicz, RH ;

Valeriote, FA ;

Crews, P .

ORGANIC LETTERS, 2004, 6 (12) :1951-1954

[2] Total Synthesis of Irciniastatin A (Psymberin) [J].

Crimmins, Michael T. ;

Stevens, Jason M. ;

Schaaf, Gregory M. .

ORGANIC LETTERS, 2009, 11 (17) :3990-3993

[3]

David M, 1998, SYNLETT, P206

[4] One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf [J].

Downey, C. Wade ;

Johnson, Miles W. ;

Tracy, Kathryn J. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3299-3302

[5] A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf [J].

Downey, C. Wade ;

Johnson, Miles W. .

TETRAHEDRON LETTERS, 2007, 48 (20) :3559-3562

[6] Acetic Acid Aldol Reactions in the Presence of Trimethylsilyl Trifluoromethanesulfonate [J].

Downey, C. Wade ;

Johnson, Miles W. ;

Lawrence, Daniel H. ;

Fleisher, Alan S. ;

Tracy, Kathryn J. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5351-5354

[7] ORGANIC CHEMISTRY USING WEAKLY ELECTROPHILIC SALTS: THE REACTION WITH NITROGEN NUCLEOPHILES [J].

Fujioka, Hiromichi ;

Kubo, Ozora ;

Senami, Kento ;

Okamoto, Kazuhisa ;

Okitsu, Takashi ;

Kita, Yasuyuki .

HETEROCYCLES, 2009, 79 :1113-1120

[8] Stereoselective Synthesis of α- and β-C-Glycosides by Addition of Titanium Enolates to Glyeals [J].

Galvez, Erik ;

Larrosa, Igor ;

Romea, Pedro ;

Urpi, Felix .

SYNLETT, 2009, (18) :2982-2986

[9] Synthesis of α-Amino Amides via N,O-Acetals Derived from Weinreb Amides [J].

Hirner, Sebastian ;

Somfai, Peter .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (20) :7798-7803

[10] MANNICH-TYPE REACTION OF N,O-ACETALS WITH KETONES MEDIATED BY A COMBINATION OF TiCl4 AND PhSiCl3 [J].

Kamogawa, Satoshi ;

Ikeda, Takashi ;

Kuriyama, Masami ;

Matsumura, Yoshihiro ;

Onomura, Osamu .

HETEROCYCLES, 2010, 82 (01) :325-332