{"doi":"10.1002/ejoc.200400614","title":"Determination of the Absolute Configuration of Inherently Chiral Resorc[4]arenes","abstract":"<jats:title>Abstract</jats:title><jats:p>The absolute configuration of twelve inherently chiral resorc‐arenes was determined using a combination of the X‐ray structure of (–)‐<jats:bold>3a</jats:bold> and optical rotation as well as NMR techniques. Starting from a racemic mixture of <jats:bold>1</jats:bold> both diastereomers (–)‐<jats:bold>3a</jats:bold> and (+)‐<jats:bold>3b</jats:bold> can be obtained in high yields in two steps and the absolute configuration of these diastereomers could be determined by X‐ray analysis. Using enantiomerically pure (–)‐<jats:bold>1</jats:bold> for the same reactions, however, (+)‐<jats:bold>3b</jats:bold> is formed. The alkylation of (–)‐<jats:bold>1</jats:bold> with (<jats:italic>S</jats:italic>)‐2‐methylbutyl tosylate and the methylation of (–)‐<jats:bold>5a</jats:bold> lead to the same resorcarene (–)‐<jats:bold>4a</jats:bold>, while the alkylation of (+)‐<jats:bold>1</jats:bold> and the methylation of (+)‐<jats:bold>5b</jats:bold> yield in resorcarene (+)‐<jats:bold>4b</jats:bold>. (© Wiley‐VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2005)</jats:p>","journal":"European Journal of Organic Chemistry","year":2005,"id":675083,"datarank":0.4887144807032224,"base_score":3.258096538021482,"endowment":3.258096538021482,"self_citation_contribution":0.4887144807032224,"citation_network_contribution":0.0,"self_endowment_contribution":0.4887144807032224,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":25,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":null,"is_data_producer":false,"deposit_databanks":null,"is_oa":false,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":null,"fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1763857,"name":"Beate Neumann","orcid":null,"position":1,"is_corresponding":false},{"id":1763858,"name":"Hans‐Georg Stammler","orcid":null,"position":2,"is_corresponding":false},{"id":1763859,"name":"Jochen Mattay","orcid":null,"position":3,"is_corresponding":false},{"id":1763856,"name":"Michael Klaes","orcid":null,"position":0,"is_corresponding":false}],"reference_count":0,"raw_metadata":{"has_enrichment":true,"resolved":true,"title":"Determination of the Absolute Configuration of Inherently Chiral Resorc[4]arenes","abstract":"<jats:title>Abstract</jats:title><jats:p>The absolute configuration of twelve inherently chiral resorc‐arenes was determined using a combination of the X‐ray structure of (–)‐<jats:bold>3a</jats:bold> and optical rotation as well as NMR techniques. Starting from a racemic mixture of <jats:bold>1</jats:bold> both diastereomers (–)‐<jats:bold>3a</jats:bold> and (+)‐<jats:bold>3b</jats:bold> can be obtained in high yields in two steps and the absolute configuration of these diastereomers could be determined by X‐ray analysis. Using enantiomerically pure (–)‐<jats:bold>1</jats:bold> for the same reactions, however, (+)‐<jats:bold>3b</jats:bold> is formed. The alkylation of (–)‐<jats:bold>1</jats:bold> with (<jats:italic>S</jats:italic>)‐2‐methylbutyl tosylate and the methylation of (–)‐<jats:bold>5a</jats:bold> lead to the same resorcarene (–)‐<jats:bold>4a</jats:bold>, while the alkylation of (+)‐<jats:bold>1</jats:bold> and the methylation of (+)‐<jats:bold>5b</jats:bold> yield in resorcarene (+)‐<jats:bold>4b</jats:bold>. (© Wiley‐VCH Verlag GmbH &amp; Co. 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