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Parallel kinetic resolution of tert-butyl (RS)-3-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl-cispentacin derivatives.

Abstract:

The double mutual kinetic resolution of tert-butyl (RS)-3-benzyl-cyclopentene-1-carboxylate with a 50 : 50 mixture of lithium (RS)-N-benzyl-N-alpha-methylbenzylamide and lithium (RS)-N-3,4-dimethoxybenzyl-N-alpha-methylbenzylamide gives, after protonation with 2,6-di-tert-butylphenol, a 50 : 50 mixture of the readily separable N-benzyl-(1SR,2RS,3RS,alphaRS)- and N-3,4-dimethoxybenzyl-(1SR,2RS,3RS,alphaRS)-beta-amino esters in >98% de in each case. This product distribution indicates that t...

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Publication status:
Published

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Publisher copy:
10.1039/b407560a

Authors


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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry More from this journal
Volume:
2
Issue:
22
Pages:
3355-3362
Publication date:
2004-11-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Language:
English
Keywords:
Pubs id:
pubs:110546
UUID:
uuid:21761ba8-ddfb-4526-ae95-5a25517dc839
Local pid:
pubs:110546
Source identifiers:
110546
Deposit date:
2012-12-19

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