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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 6
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Original Articles

Enantioselective Synthesis of Chiral Propargylic Alcohols Catalyzed by Bifunctional Zinc-Based Complexes

, , , &
Pages 775-783 | Received 17 Nov 2009, Published online: 11 Nov 2011
 

Abstract

This work demonstrates an efficient way to prepare chiral propargylic alcohols by asymmetric addition of terminal Zn-acetylide to aldehydes catalyzed by bifunctional zinc-based complexes. The corresponding products with moderate to good yields and enantioselectivities were obtained in the absence of moisture-sensitive Ti(O i Pr)4.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

We are grateful to the grants from the National Natural Science Foundation of China (No. 20802046), International S&T Cooperation Program of Jiangsu Province (BZ2010048), the Priority Academic Program Development of Jiangsu Higher Education Institutions, and the Key Laboratory of Organic Synthesis of Jiangsu Province for financial support.

Notes

a All the reactions were performed under argon at room temperature for 24 h. Alkyne/Me2Zn/benzaldehyde/ligand 1:1:0.5:0.05.

b Isolated yield.

c The enantiomeric excess was determined by chiral HPLC analysis of the corresponding products on a Chiralcel OD-H column.

d 0.2 mmol Ti(O i Pr)4 was used.

e 1 mmol HMPA was added.

f 1 mmol DME was added.

g Reaction was carried out at 0 °C.

h Reaction was carried out at 60 °C.

a All the reactions were performed under argon at room temperature for 24 h. Alkyne/Et2Zn/benzaldehyde/C 1:1:0.5:0.05.

b Isolated yield.

c The enantiomeric excess was determined by chiral HPLC analysis of the corresponding products on a Chiralcel OD-H column.

d The ee in parentheses was determined after simple recrystallization.

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