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.
Links
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 -