REGIOSELECTIVITY OF THE REACTION OF ORGANOZINC COMPOUNDS WITH ALPHA-IMINOESTERS DERIVED FROM 2-AMINO OR 3-AMINO ALCOHOLS .2. SYNTHESIS OF 3-SUBSTITUTED HEXAHYDRO-1,4-OXAZEPIN-2-ONES AND TETRAHYDRO-1,4-OXAZIN-2-ONES

被引：5

作者：

COURTOIS, G ^{[1
]}

MIGINIAC, L ^{[1
]}

机构：

[1] UNIV POITIERS,CNRS,UA 574,SYNTHESE ORGAN LAB,40 AVE RECTEUR PINEAU,F-86022 POITIERS,FRANCE

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1993年 / 452卷 / 1-2期

关键词：

D O I：

10.1016/0022-328X(93)83164-Q

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The preparation of some alpha-iminoesters R'N=CHCOOCH3 with R' bearing an alcohol group has been studied; organozinc compounds prepared from allylic or propargylic bromides and from alpha-bromoesters or alpha-bromoamides react regiospecifically with these alpha-iminoesters to give polyfunctional alpha-aminoesters. Some of them are easily converted into tetrahydro-1,4-oxazin-2-ones and hexahydro-1,4-oxazepin-2-ones.

引用

页码：5 / 12

页数：8

共 45 条

[1] REGIOSELECTIVITY OF THE REACTION OF ORGANOZINC COMPOUNDS WITH ALPHA-IMINO ESTERS FROM 2-AMINO AND 3-AMINO ALCOHOLS .1. SYNTHESIS OF POLYFUNCTIONAL ALPHA-AMINO ESTERS
COURTOIS, G
MIGINIAC, L
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1993, 450 (1-2) : 33 - 40
[2] SYNTHESIS OF 3,5-DIHALOGENO-2H-1,4-OXAZIN-2-ONES FROM CYANOHYDRINS
MEERPOEL, L
HOORNAERT, G
TETRAHEDRON LETTERS, 1989, 30 (24) : 3183 - 3186
[3] SYNTHESIS OF 3-AMINO-1,4-DIARYLAZETIDIN-2-ONES .2.
DAVE, MA
KELUSKAR, CV
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1995, 72 (10) : 727 - 729
[4] A GENERAL-SYNTHESIS OF 3,5-DIHALO-2H-1,4-OXAZIN-2-ONES FROM CYANOHYDRINS
MEERPOEL, L
HOORNAERT, G
SYNTHESIS-STUTTGART, 1990, (10): : 905 - 908
[5] CYCLOADDITION OF OLEFINIC COMPOUNDS TO 2H-1,4-OXAZIN-2-ONES - SYNTHESIS OF 2-OXA-5-AZABICYCLO[2.2.2]OCT-5-EN-3-ONES
FANNES, C
MEERPOEL, L
TOPPET, S
HOORNAERT, G
SYNTHESIS-STUTTGART, 1992, (07): : 705 - 709
[6] Chiral 3,6-dihydro-2H-1,4-oxazin-2-ones as alanine equivalents for the asymmetric synthesis of α-methyl α-amino acids (AMAAs) under mild reaction conditions
Chinchilla, R
Galindo, N
Nájera, C
SYNTHESIS-STUTTGART, 1999, (04): : 704 - 717
[7] A convenient two-step synthesis of amino acid derived chiral 3-substituted [1,4]benzodiazepin-2-ones
Mishra, JK
Panda, G
SYNTHESIS-STUTTGART, 2005, (11): : 1881 - 1887
[8] CYCLOADDITIONS OF 3-AMINO-2H-1,4-OXAZIN-2-ONES WITH OLEFINS - GENERATION OF 5,6-DIHYDRO-2-OXO-2H-PYRAN-6-CARBONITRILES
FANNES, CC
HOORNAERT, GJ
TETRAHEDRON LETTERS, 1992, 33 (15) : 2049 - 2052
[9] THE SYNTHESIS OF 3-FUNCTIONALIZED 5-CHLORO-6-METHYL-2H-1,4-OXAZIN-2-ONES AND OF PYRIDINES FROM CYCLOADDITION-ELIMINATION REACTIONS WITH SUBSTITUTED ACETYLENIC-COMPOUNDS
VANAKEN, KJ
LUX, GM
DEROOVER, GG
MEERPOEL, L
HOORNAERT, GJ
TETRAHEDRON, 1994, 50 (17) : 5211 - 5224
[10] Asymmetric synthesis of (S)-α-methyl α-amino acids by alkylation of chiral 3,6-dihydro-2H-1,4-oxazin-2-ones using unactivated alkyl halides and organic bases
Chinchilla, R
Galindo, N
Nájera, C
TETRAHEDRON-ASYMMETRY, 1998, 9 (16) : 2769 - 2772

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