Alternatives to allylstannanes for remote stereocontrol

Pure and Applied Chemistry

Volumn 78, Issue 11, 2006, Pages 2015-2028

  Booth, Matthew ^a   Brain, Christopher ^a   Castreno, Pilar ^a   Donnelly, Sam ^a   Dorling, E Kate ^a   Germay, Olivier ^a   Hobson, Lindsay ^a   Kumar, Naresh ^a   Martin, Nathaniel ^a   Moore, Christopher ^a   Negi, Devendra ^a   Thomas, Eric J ^a   Weston, Anna ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Allylmetals; Bismuth; Organostannane; Stereoselectivity; Synthesis

Indexed keywords

EID: 33750913677     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200678112015     Document Type: Conference Paper

References (31)

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21. The reaction between the allyltin trichlorides and aldehydes may involve a six-membered transition structure with an octahedral tin. Alternatively, the aldehyde may displace the oxygen substituent from the tin followed by a metallo-ene type process via a transition structure with the group α to tin in the axial position, cf. transition structure 6. This process explains the strong preference for cis-alkene formation in all cases.
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24. (E)-Alk-2-enylstannanes have usually been used in tin(IV) halide-promoted reactions with aldehydes and useful stereoselectivities obtained, vide supra. However, it may be that even better stereoselectivities would have been observed had (Z)-alk-2-enylstannanes been used.
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30. The different stereoselectivities for the tin(IV) halide- and bismuth(III) iodide-promoted reactions of allylstannanes indicate that different mechanisms are involved. In Scheme 20, a cyclic transition structure 70 is proposed for the reaction between the alkenylbismuth di-iodide 69 and an aldehyde. However, an open-chain process, e.g., one involving an antiperiplanar arrangement of the terminal allylbismuth di-iodide 69 and the aldehyde carbonyl group, which is antarafacial with respect to the allylbismuth di-iodide, would also be compatible with the observed stereoselectivity. Alternatively, a bismuthate species might be involved which would have to react via an open-chain process. As the stereoselectivities of more allyllic bromides in this reaction are investigated, it may be possible to decide between cyclic and open-chain processes.
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