Diastereo- and enantioselective synthesis of 2,8-dioxabicyclo[3.3.0]octan-3-one derivatives

Abstract

An efficient asymmetric synthesis of 4-substituted (1S,4S,5R)-2,8-dioxabicyclo[3.3.0]octan-3-one derivatives (de ⩾98%, ee = 80–>98%) in good overall yields is reported by a stepwise Michael addition–α-alkylation and subsequent hydrolytic domino reaction protocol employing formaldehyde SAMP-hydrazone as a neutral formyl anion equivalent and 5,6-dihydro-2H-pyran-2-one as a Michael acceptor.

References

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