(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde

Uses

Reactant for:

• Proline-catalyzed Diels Alder reaction
• Stereodivergent synthesis of carbahexofuranoses employing a Wittig olefination-Claisen rearrangement protocol
• Wittig reactions
• Crotylation reactions
• Asymmetric synthesis of Goniothalesdiol A via stereocontrolled allylation and base-catalyzed oxy-Michael addition

Synthesis

General procedure for the synthesis of (R)-1,4-dioxaspiro[4,5]decane-2-carbaldehyde from 1,2:5,6-di-O-cyclohexylidene-D-mannitol: a solution of sodium meta-periodide (NaIO4, 7.3 g, 34 mmol) and tetrabutylammonium bromide (phase transfer catalyst, 0.2 g, 0.62 mmol) in water (60 mL) was slowly added to a solution of 1,2. 5,6-di-O-cyclohexylidene-D-mannitol (10.0 g, 29.3 mmol) to a solution of tetrahydrofuran (THF, 100 mL). The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the organic layer was separated and the aqueous layer was extracted with ether (3 x 35 mL). The combined ether extracts were washed with water (1 x 35 mL) and dried with anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give a colorless viscous liquid (R)-1,4-dioxaspiro[4,5]decane-2-carboxaldehyde (compound (R)-8) in 90% yield (8.94 g).

References

[1] Synlett, 2011, # 8, p. 1154 - 1156
[2] Helvetica Chimica Acta, 2015, vol. 98, # 6, p. 823 - 833
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 36, p. 6195 - 6207
[4] Tetrahedron Letters, 2013, vol. 54, # 48, p. 6420 - 6422
[5] Organic Letters, 2017, vol. 19, # 16, p. 4167 - 4170