Esters of Pyromellitic Acid. Part II. Esters of Chiral Alcohols: Para Pyromellitate Diesters as a Novel Class of Resolving Agents and Use of Pyromellitates as Duplicands for Chiral Purification.

Esters of Pyromellitic Acid. Part II. Esters of Chiral Alcohols: Para Pyromellitate Diesters as a Novel Class of Resolving Agents and Use of Pyromellitates as Duplicands for Chiral Purification. Research Abstract Details 

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Esters of Pyromellitic Acid. Part II. Esters of Chiral Alcohols: Para Pyromellitate Diesters as a Novel Class of Resolving Agents and Use of Pyromellitates as Duplicands for Chiral Purification. Abstract Text:

Methods are presented for the preparation of pyromellitate esters of chiral terpene alcohols, including d- ( 3) or l-menthol (4), d-isomenthol ( 7), l-borneol ( 8), or d- ( 5) or l-isopinocampheol ( 6). Alcoholysis of PMDA in CH 2Cl 2/Et 3N led to the formation of monoesters (e.g., 18) or diesters ( 11, 12), as needed, relying on the differential reactivity of the two anhydride groups. The easily isolated para diester ( 11) crystallized before the meta diester ( 12) from HOAc. Nicotine ( 1, 14) was efficiently resolved as 1:1 salts with the menthyl ( 11a, 11b) or bornyl ( 11f) para diesters, prototypes of what promises to be a large class of novel resolving agents. Recrystallization of para-di- d-menthyl pyromellitate ( 11a) greatly improved the chiral purity of the contained d-menthol ( 3), an example of purification by "duplication". An alternative synthesis of specific diesters took advantage of the easily separated benzyl diesters and their derived acid chlorides ( 19, 21), with the benzyl esters serving as temporary blocking groups removable by catalytic hydrogenolysis. Pyromellitate tetraesters ( 26) were prepared by base-catalyzed transesterification of the tetraethyl ester ( 25). Tri- l-menthyl pyromellitate ( 27b) was obtained by catalytic hydrogenolysis of benzyl tri- l-menthyl pyromellitate ( 31b), itself prepared from the alcoholysis of benzyl pyromellitate triacid chloride ( 30) with l-menthol ( 4).

Esters of Pyromellitic Acid. Part II. Esters of Chiral Alcohols: Para Pyromellitate Diesters as a Novel Class of Resolving Agents and Use of Pyromellitates as Duplicands for Chiral Purification. Publishing Authors By Initials

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Esters of Pyromellitic Acid. Part II. Esters of Chiral Alcohols: Para Pyromellitate Diesters as a Novel Class of Resolving Agents and Use of Pyromellitates as Duplicands for Chiral Purification. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 73

Page Numbers: 4939-48

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 4

MONTH: 06

YEAR: 2008

Esters of Pyromellitic Acid. Part II. Esters of Chiral Alcohols: Para Pyromellitate Diesters as a Novel Class of Resolving Agents and Use of Pyromellitates as Duplicands for Chiral Purification. Information

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LANGUAGE: eng

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