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Asymmetric transformation of L-homoserine lactone to an optically active 2-substituted pyrrolidine for clemastine
- Kim, Seung Jin;
- Chang, Minsun;
- Kim, Hee-Doo
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6초록
The asymmetric transformation of L-homoserine lactone to (R)-ethyl 2-(2-chloroethyl)pyrrolidine-1-carboxylate for clemastine has been accomplished by a combination of regioselective N-allylation and ring-closing metathesis. A key feature associated with the synthesis involved the racemization-minimized N-allylation of carbamate version of an amino ester by using P4-phosphazene as a base. This method might offer an alternative route to obtain optically active 2-substituted pyrrolidines from alpha-amino esters, not easily accessible from proline-based asymmetric transformations. (C) 2011 Elsevier Ltd. All rights reserved.
키워드
RING-CLOSING METATHESIS; STEREOSELECTIVE-SYNTHESIS; NOBEL LECTURE; ABSOLUTE-CONFIGURATION; OLEFIN-METATHESIS; DERIVATIVES; ALKALOIDS; ACID; DIALLYLAMINES; INTERMEDIATE
- 제목
- Asymmetric transformation of L-homoserine lactone to an optically active 2-substituted pyrrolidine for clemastine
- 저자
- Kim, Seung Jin; Chang, Minsun; Kim, Hee-Doo
- 발행일
- 2011-11-30
- 유형
- Article
- 권
- 22
- 호
- 20-22
- 페이지
- 1901 ~ 1905