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Direct asymmetric catalytic thienylaluminum addition to ketones: a concise approach to the synthesis of (S)-tiemonium iodide.
Org Lett. 2009 Aug 06; 11(15):3386-9.OL

Abstract

A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-acetylcyclohexene, furnishing products in excellent enantioselectivities of up to 97% ee. However, the additions to dialkyl ketones afford products in low enantioselectivities of 8-17% ee. Importantly, a concise 3-step synthesis of (S)-tiemonium iodide with an 84% yield is demonstrated.

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Authors+Show Affiliations

Biradar DB
Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.
Zhou S
No affiliation info available
Gau HM
No affiliation info available

MeSH

AlcoholsAluminumCatalysisCyclohexenesKetonesMorpholinesNaphtholsTitanium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19588914

Citation

Biradar, Deepak B., et al. "Direct Asymmetric Catalytic Thienylaluminum Addition to Ketones: a Concise Approach to the Synthesis of (S)-tiemonium Iodide." Organic Letters, vol. 11, no. 15, 2009, pp. 3386-9.
Biradar DB, Zhou S, Gau HM. Direct asymmetric catalytic thienylaluminum addition to ketones: a concise approach to the synthesis of (S)-tiemonium iodide. Org Lett. 2009;11(15):3386-9.
Biradar, D. B., Zhou, S., & Gau, H. M. (2009). Direct asymmetric catalytic thienylaluminum addition to ketones: a concise approach to the synthesis of (S)-tiemonium iodide. Organic Letters, 11(15), 3386-9. https://doi.org/10.1021/ol901193q
Biradar DB, Zhou S, Gau HM. Direct Asymmetric Catalytic Thienylaluminum Addition to Ketones: a Concise Approach to the Synthesis of (S)-tiemonium Iodide. Org Lett. 2009 Aug 6;11(15):3386-9. PubMed PMID: 19588914.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Direct asymmetric catalytic thienylaluminum addition to ketones: a concise approach to the synthesis of (S)-tiemonium iodide. AU - Biradar,Deepak B, AU - Zhou,Shuangliu, AU - Gau,Han-Mou, PY - 2009/7/11/entrez PY - 2009/7/11/pubmed PY - 2009/12/16/medline SP - 3386 EP - 9 JF - Organic letters JO - Org Lett VL - 11 IS - 15 N2 - A direct asymmetric addition of a (2-thienyl)aluminum reagent to ketones catalyzed by a titanium catalyst of (S)-BINOL to afford chiral tertiary 2-thienyl alcohols is reported. The catalytic system works excellently for aromatic ketones and for 1-acetylcyclohexene, furnishing products in excellent enantioselectivities of up to 97% ee. However, the additions to dialkyl ketones afford products in low enantioselectivities of 8-17% ee. Importantly, a concise 3-step synthesis of (S)-tiemonium iodide with an 84% yield is demonstrated. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19588914/Direct_asymmetric_catalytic_thienylaluminum_addition_to_ketones:_a_concise_approach_to_the_synthesis_of__S__tiemonium_iodide_ L2 - https://doi.org/10.1021/ol901193q DB - PRIME DP - Unbound Medicine ER -