1986
DOI: 10.1016/s0040-4020(01)82096-2
|View full text |Cite
|
Sign up to set email alerts
|

Stereoselective synthesis of polyols precursors by allyl sulphinyl anion addition to chiral alkoxy aldehydes

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
9
0

Year Published

1987
1987
2019
2019

Publication Types

Select...
4
1
1

Relationship

0
6

Authors

Journals

citations
Cited by 9 publications
(9 citation statements)
references
References 18 publications
0
9
0
Order By: Relevance
“…2 [33,34]. The products were identified by comparison with published 1 H and 13 C NMR data [35][36][37][38][39]. [33,34] A representative 1 H NMR spectrum of the bis-ketal (3b), ketal-ether (4b) product mixture from the Amberlite-15 catalyzed reaction of meso-erythritol (1), with acetone (2b) is shown in Fig.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…2 [33,34]. The products were identified by comparison with published 1 H and 13 C NMR data [35][36][37][38][39]. [33,34] A representative 1 H NMR spectrum of the bis-ketal (3b), ketal-ether (4b) product mixture from the Amberlite-15 catalyzed reaction of meso-erythritol (1), with acetone (2b) is shown in Fig.…”
Section: Resultsmentioning
confidence: 99%
“…90-91 °C (Lit. 89-90 °C [37]). The crystal of 3f (C 16 H 20 O 4 , M = 282.37) is orthorhombic, space group Pbca, at T = 100 K: a = 8.3505(18) Å, b = 7.5675(17) Å, c = 23.461(5) Å, α, β, γ = 90°, V = 1482.6(6) Å 3 , Z = 4, d calc = 1.265 g/cm 3 , F(000) = 616, μ = 0.089 mm −1 .…”
Section: X-ray Structure Determination Of 3fmentioning
confidence: 99%
“…TIPSprotected 15 was prepared in a similar way to the synthesis of 7β. Colorless oil (121 mg, 0.293 mmol, 68%), [α] 25 D −16.2 (c 1.00, CHCl 3 ); IR (neat) 3456, 2931, 2862, 1466, 1250, 1134 cm −1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 0.88 (t, J = 6.9 Hz, 3H), 1.04−1.11 (m, 21H), 1.17 (d, J = 5.8 Hz, 3H), 1.22−1.41 (m, 18H), 2.04 (dt, J = 6.9, 6.9 Hz, 2H), 2.69 (br d, J = 3.2 Hz, 1H), 3.74−3.84 (m, 2H), 5.42 (dd, J = 15.4, 6.7 Hz, 1H), 5.74 (dt, J = 15.4, 6.9 Hz, 1H); 13 C NMR (125 MHz, CDCl 3 ) δ 12.6 (CH), 12.6 (CH), 12.6 (CH), 14.1 (CH 3 ), 18.07 (CH 3 ), 18.07 (CH 3 ), 18.07 (CH 3 ), 18.14 (CH 3 ), 18.14 (CH 3 ), 18.14 (CH 3 ), 20 (4R,5R,E)-4,5-Bis((tert-butyldimethylsilyl)oxy)hex-2-en-1-ol (16). A mixture of 3 (119 mg, 0.685 mmol), TBSCl (372 mg, 2.47 mmol), imidazole (237 mg, 3.49 mmol), and DMAP (8.70 mg, 0.0712 mmol) in DMF (7.0 mL) was stirred at room temperature for 14.5 h and additionally stirred at 80 °C for 12.5 h. After the addition of H 2 O (10 mL) at 0 °C, the mixture was extracted with hexane/ EtOAc (2/1, 10 mL × 3), dried over MgSO 4 , and concentrated under reduced pressure.…”
mentioning
confidence: 99%
“…[α] 25 D −17.6 (c 1.00, CHCl 3 ); IR (neat) 3348, 2954, 2931, 2854, 1257, 1095 cm −1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 0.09 (s, 3H), 0.09 (s, 3H), 0.90 (s, 9H), 1.16 (d, J = 6.1 Hz, 3H), 1.39 (t, J = 5.8 Hz, 1H), 2.62 (d, J = 4.2 Hz, 1H), 3.67 (qd, J = 6.1, 6.1 Hz, 1H), 3.85 (dddd, J = 6.5, 6.1, 4.2, 1.1 Hz, 1H), 4.17 (dd, J = 5.8, 5.2 Hz, 2H), 5.69 (ddt, J = 15.5, 6.5, 1.5 Hz, 1H), 5.95 (dtd, J = 15.5, 5.2, 1.1 Hz, 1H); 13 C NMR (125 MHz, CDCl 3 ) δ −4.9 (CH 3 ), −4.3 (CH 3 ), 18.0 (C), 19.9 (CH 3 ), 25.8 (CH 3 ), 25.8 (CH 3 ), 25.8 (CH 3 ), 62.9 (CH 2 ), 71.8 (CH), 76.4 (CH), 130. 20 TBS-protected diol 17α was prepared from the enantiomer of 3 (ethyl (2E,4S,5S)-4,5-dihydroxy-2-hexenoate) in a similar way to the synthesis of 17β. The intermediate allyl alcohol 23 (ethyl (2E,4S,5S)-5-((tert-butyldimethylsilyl)oxy)-4-hydroxy-2-hexenoate), 19 Colorless oil (2.84 g, 9.85 mmol, 37%), [α] 25 D +4.6 (c 1.00, CHCl 3 ); IR (neat) 3479, 2954, 2931, 1720, 1257, 1095 cm −1 ; 1 H NMR (300 MHz, CDCl 3 ) δ 0.06 (s, 3H), 0.08 (s, 3H), 0.89 (s, 9H), 1.22 (d, J = 6.2 Hz, 3H), 1.29 (t, J = 7.1 Hz, 3H), 2.60 (d, J = 5.8 Hz, 1H), 3.77 (qd, J = 6.2, 5.0 Hz, 1H), 4.02 (dddd, J = 5.8, 5.0, 4.6, 1.7 Hz, 1H), 4.20 (q, J = 7.1 Hz, 2H), 6.12 (dd, J = 15.6, 1.7 Hz, 1H), 6.90 (dd, J = 15.6, 4.6 Hz, 1H); 13 C NMR (150 MHz, CDCl 3 ) δ −4.9 (CH 3 ), −4.4 (CH 3 ), 14.2 (CH 3 ), 18.0 (C), 20 (2S,3S,E)-Hexadec-4-ene-2,3-diol (19).…”
mentioning
confidence: 99%
See 1 more Smart Citation