ABSOLUTE ASYMMETRIC-SYNTHESIS BY IRRADIATION OF CHIRAL CRYSTALS

被引：37

作者：

KAUPP, G

HAAK, M

机构：

[1] Organische Chemie I, Universität Oldenburg, D-W-2900

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 05期

关键词：

D O I：

10.1002/anie.199306941

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

When achiral molecules crystallize in chiral space group and irradiation of the crystals furnishes chiral products, one may speak of absolute asymmetric synthesis that is synthesis without the use of chiral auxiliaries. In the reaction of 1 to yield 2 Sakamoto et al. recently discovered an intramolecular absolute asymmetric synthesis. Without external seeding for the crystallization optically active 2 forms with up to 40% ee. This finding should provide new horizons for previously well-trodden paths.

引用

收藏

页码：694 / 695

页数：2

相关论文

共 19 条

[1] PHOTO-POLYMERIZATION IN CHIRAL CRYSTALS .4. ENGINEERING OF CHIRAL CRYSTALS FOR ASYMMETRIC (2-PI + 2-PI) PHOTO-POLYMERIZATION - EXECUTION OF AN ABSOLUTE ASYMMETRIC-SYNTHESIS WITH QUANTITATIVE ENANTIOMERIC YIELD [J].

ADDADI, L ;

VANMIL, J ;

LAHAV, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) :3422-3429

[2] DIFFERENCES IN PHOTOCHEMICAL REACTIVITY OF 9,10-ETHENOANTHRACENE DERIVATIVES IN LIQUID AND CRYSTALLINE MEDIA [J].

CHEN, JX ;

SCHEFFER, JR ;

TROTTER, J .

TETRAHEDRON, 1992, 48 (16) :3251-3274

[3] USE OF CHIRAL SINGLE-CRYSTALS TO CONVERT ACHIRAL REACTANTS TO CHIRAL PRODUCTS IN HIGH OPTICAL YIELD - APPLICATION TO THE DI-PI-METHANE AND NORRISH TYPE-II PHOTOREARRANGEMENTS [J].

EVANS, SV ;

GARCIAGARIBAY, M ;

OMKARAM, N ;

SCHEFFER, JR ;

TROTTER, J ;

WIREKO, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (18) :5648-5650

[4] ENANTIOSELECTIVE PHOTOREACTIONS OF CYCLOOCTA-2,4,6-TRIEN-1-ONE AND CYCLOOCTA-2,4-DIEN-1-ONE IN THEIR INCLUSION COMPLEXES WITH (R,R)-(-)-1,6-BIS(O-CHLOROPHENYL)-1,6-DIPHENYLHEXA-2,4-DIYNE-1,6-DIOL - MECHANISTIC STUDY BASED ON X-RAY CRYSTAL-STRUCTURE ANALYSES [J].

FUJIWARA, T ;

NANBA, N ;

HAMADA, K ;

TODA, F ;

TANAKA, K .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4532-4537

[5] REACTIONS IN CHIRAL CRYSTALS - PRINCIPLES GOVERNING ASYMMETRIC SYNTHESIS VIA TOPOCHEMICALLY CONTROLLED SOLID-STATE PHOTO-DIMERIZATION [J].

GREEN, BS ;

LAHAV, M ;

SCHMIDT, GMJ .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1975, 29 (3-4) :187-200

[6] KALEIDOSCOPIC PHOTOCHEMICAL BEHAVIOR OF UNSYMMETRIC DIOLEFIN CRYSTALS [J].

HASEGAWA, M ;

HASHIMOTO, Y .

MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1992, 219 :1-15

[7] PHOTODIMERIZATION OF ANTHRACENES IN THE SOLID-STATE - NEW RESULTS FROM ATOMIC FORCE MICROSCOPY [J].

KAUPP, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (05) :595-598

[8] PHOTODIMERIZATION OF CINNAMIC ACID IN THE SOLID-STATE - NEW INSIGHTS ON APPLICATION OF ATOMIC FORCE MICROSCOPY [J].

KAUPP, G .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (05) :592-595

[9]

Kaupp G., 1992, ANGEW CHEM, V104, P609

[10]

KAUPP G, 1992, ANGEW CHEM, V104, P606