One-pot synthesis of γ-hydroxy-γ-oxaphosphonates using pentacovalent oxaphosphorane chemistry

被引:4
作者
Hwang, Jae-Min [2 ]
Islam, Tasneem [1 ]
Jung, Kang-Yeoun [2 ]
机构
[1] Roosevelt Univ, Dept Biol Chem & Phys Sci, Chicago, IL 60173 USA
[2] Kangnung Wonju Natl Univ, Coll Engn, Dept Environm & Appl Chem, Kangnung 210702, South Korea
关键词
Phosphonates; Oxaphospholene; Enolate; Aldol product; ORGANIC-SYNTHESIS; PHOSPHONATES; ANALOGS; ROUTE;
D O I
10.1016/j.tetlet.2009.08.059
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
P(V)-2,2,2-triethoxy-2,2-dihydro-5-methoxy-1,2 lambda(5)-oxaphospholene was synthesized as a new type of enolate which was hydrolyzed to give a series of phosphonates. In addition, aldol reaction of the oxaphospholene intermediate with several aldehydes as electrophiles under mild and neutral conditions produced phosphonate-containing aldol compounds through a two-step one-pot reaction. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6076 / 6078
页数:3
相关论文
共 15 条
[1]   A CONVENIENT SYNTHETIC ROUTE TO N-ARYL AND N-ALKYLAMINO(ALKYL) PHOSPHONATES AND PHOSPHINE OXIDES [J].
COUTURE, A ;
DENIAU, E ;
WOISEL, P ;
GRANDCLAUDON, P .
TETRAHEDRON LETTERS, 1995, 36 (14) :2483-2486
[2]   PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES [J].
ENGEL, R .
CHEMICAL REVIEWS, 1977, 77 (03) :349-367
[3]  
Eto M., 1992, HDB ORGANOPHOSPHORUS, P807
[4]   Synthesis of natural products containing a C-P bond [J].
Fields, SC .
TETRAHEDRON, 1999, 55 (42) :12237-12272
[5]  
Hwang JM, 2009, B KOREAN CHEM SOC, V30, P239
[6]   REGIOSELECTIVE AND STEREOSELECTIVE CROSS-ALDOL REACTIONS VIA DIALKYLBORYL TRIFLATES [J].
INOUE, T ;
MUKAIYAMA, T .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1980, 53 (01) :174-178
[7]  
KALIR A, 1996, CHEM ORGANOPHOSPHORU, V4, P767
[8]   A NEW CLASS OF ACYCLIC PHOSPHONATE NUCLEOTIDE ANALOGS - PHOSPHONATE ISOSTERES OF ACYCLOVIR AND GANCICLOVIR MONOPHOSPHATES AS ANTIVIRAL AGENTS [J].
KIM, CU ;
MISCO, PF ;
LUH, BY ;
HITCHCOCK, MJM ;
GHAZZOULI, I ;
MARTIN, JC .
JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :2286-2294
[9]   PENTACOVALENT PHOSPHORUS IN ORGANIC-SYNTHESIS - A NEW ROUTE TO SUBSTITUTED PHOSPHONATES [J].
MCCLURE, CK ;
JUNG, KY ;
GROTE, CW ;
HANSEN, K .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 75 (1-4) :23-26
[10]   PENTACOVALENT OXAPHOSPHORANE CHEMISTRY IN ORGANIC-SYNTHESIS .2. TOTAL SYNTHESES OF (+/-)-TRANS-NEOCNIDILIDE AND (+/-)-CIS-NEOCNIDILIDE [J].
MCCLURE, CK ;
JUNG, KY .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2326-2332