ASYMMETRIC ALDOL REACTIONS EMPLOYING A CAMPHOR-DERIVED CHIRAL OXAZINONE AUXILIARY

被引：33

作者：

AHN, KH ^{[1
]}

LEE, SK ^{[1
]}

LIM, AK ^{[1
]}

机构：

[1] POHANG INST SCI & TECHNOL,CTR BIOFUNCT MOLECULES,POHANG 790600,SOUTH KOREA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 19期

关键词：

D O I：

10.1021/jo00045a010

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The aldol reactions of triisopropoxytitanium enolate of camphor-derived N-propionyloxazinone 6 with representative aldehydes afforded "chelation-controlled" syn aldols with excellent stereoselection (99:less-than-or-equal-to 1).

引用

页码：5065 / 5066

页数：2

共 20 条

[11]

HEATHCOCK CH, 1984, ASYMMETRIC SYNTHESIS, V3, P111

[12]

IKOTA N, 1986, CHEM PHARM BULL, V34, P1050

[13] ORGANOALUMINUM-PROMOTED BECKMANN REARRANGEMENT OF OXIME SULFONATES [J].

MARUOKA, K ;

MIYAZAKI, T ;

ANDO, M ;

MATSUMURA, Y ;

SAKANE, S ;

HATTORI, K ;

YAMAMOTO, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2831-2843

[14] ASYMMETRIC ALDOL REACTIONS - USE OF THE TITANIUM ENOLATE OF A CHIRAL N-ACYLOXAZOLIDINONE TO REVERSE DIASTEREOFACIAL SELECTIVITIES [J].

NERZSTORMES, M ;

THORNTON, ER .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2489-2498

[15] APPARENT CHELATION CONTROL IN ALDOL REACTIONS OF CHIRAL (ME2CHO)3TI-ENOLATES [J].

NERZSTORMES, M ;

THORNTON, ER .

TETRAHEDRON LETTERS, 1986, 27 (08) :897-900

[16] BORNANESULTAM-DIRECTED ASYMMETRIC-SYNTHESIS OF CRYSTALLINE, ENANTIOMERICALLY PURE SYN ALDOLS [J].

OPPOLZER, W ;

BLAGG, J ;

RODRIGUEZ, I ;

WALTHER, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2767-2772

[17] SINGLE-POT REDUCTIVE CONVERSION OF AMINO-ACIDS TO THEIR RESPECTIVE 2-OXAZOLIDINONES EMPLOYING TRICHLOROMETHYL CHLOROFORMATE AS THE ACYLATING AGENT - A MULTIGRAM SYNTHESIS [J].

PRIDGEN, LN ;

PROL, J ;

ALEXANDER, B ;

GILLYARD, L .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) :3231-3233

[18] 1,3-ASYMMETRIC INDUCTION IN ADDITION-REACTIONS OF CHIRAL BETA-ALKOXY ALDEHYDES - EFFICIENT CHELATION CONTROL VIA LEWIS ACIDIC TITANIUM REAGENTS [J].

REETZ, MT ;

JUNG, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (14) :4833-4835

[19] ACYCLIC STEREOSELECTION .54. EXTENDING THE SCOPE OF THE EVANS ASYMMETRIC ALDOL REACTION - PREPARATION OF ANTI-ALDOLS AND NON-EVANS SYN-ALDOLS [J].

WALKER, MA ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (20) :5747-5750

[20]

YAN TH, 1991, TETRAHEDRON LETT, V2, P5563

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