1990
DOI: 10.1021/jo00306a019
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Enantiomerically pure ketals: diastereofacial selectivity in the halogenation of enol ethers

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Cited by 33 publications
(10 citation statements)
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“…There are 10 crystal structures of esters bearing one substituent R 0 (R 00 = H) at the 2-position of the 1,3-dioxolane fragment (acetals): CSD refcodes DAZJET (Lee et al, 1999), LACREM, LACRUC (Roush et al, 1992), LEPHAR, LEPHEV (Eissmann et al, 2012), OLEGAN (Karisalmi et al, 2003), WEGXOW (Belokon' et al, 2005), XEYSEA (Jiang et al, 2007), YAXHIQ (Lv et al, 2012) and YIVGUF (Barrett et al, 1995). The crystal structures of esters with two substituents R 0 and R 00 (ketals) are represented by GAGHAY, GUHGUL (Pelphrey et al, 2004), KEMRID (Wink & Dewan, 1990), MIWDIF (Ates & Curran, 2001), NAFWEW (Mikołajczyk et al, 1996), QOTVUQ (Maezaki et al, 2000), VICXOU/ VICXOU10 (Giordano et al, 1990;Ianelli et al, 1992), VIHVAL (Linker et al, 2013) The packing of (I) parallel to (010). Two interacting molecular layers are shown.…”
Section: Tablementioning
confidence: 99%
“…There are 10 crystal structures of esters bearing one substituent R 0 (R 00 = H) at the 2-position of the 1,3-dioxolane fragment (acetals): CSD refcodes DAZJET (Lee et al, 1999), LACREM, LACRUC (Roush et al, 1992), LEPHAR, LEPHEV (Eissmann et al, 2012), OLEGAN (Karisalmi et al, 2003), WEGXOW (Belokon' et al, 2005), XEYSEA (Jiang et al, 2007), YAXHIQ (Lv et al, 2012) and YIVGUF (Barrett et al, 1995). The crystal structures of esters with two substituents R 0 and R 00 (ketals) are represented by GAGHAY, GUHGUL (Pelphrey et al, 2004), KEMRID (Wink & Dewan, 1990), MIWDIF (Ates & Curran, 2001), NAFWEW (Mikołajczyk et al, 1996), QOTVUQ (Maezaki et al, 2000), VICXOU/ VICXOU10 (Giordano et al, 1990;Ianelli et al, 1992), VIHVAL (Linker et al, 2013) The packing of (I) parallel to (010). Two interacting molecular layers are shown.…”
Section: Tablementioning
confidence: 99%
“…Colourless oil (yield 95%, 85% de) (Found M ϩ , 507.9750. C 18 H 22 79 Br 2 O 7 requires 507.9732); ν max (film)/cm Ϫ1 1766, 1737; δ H (250 MHz; CDCl 3 ) 0.95 (6H, d, J 7, (CH 3 ) 2 CH), 1.80 (1H, m, CH(CH 3 ) 2 ), 3.60, 3.80, 3.90 (3 × 3H, 3 × s, ArOCH 3 and 2 × CO 2 CH 3 ), 4.25 (1H,d,J 2,CHBr),4.85 (1H,d,J 6,OCH),4.95 (1H,d,J 6,OCH),6.85 (1H,d,J 9,ArH),7.45 (1H,dd,J 9,2,ArH),7.70 (1H,d,J 2,ArH); δ C (62.5 MHz; CDCl 3 ) 17.9, 23. 5, 29.2, 53.3, 56.6, 68.2, 79.1, 111.6, 113.3, 127.4, 130.4, 131.9, 134.7, 156.7 and 168.9.…”
Section: Dimethyl (4r5r)-2-(3-bromo-4-methoxyphenyl)-2-[(s)-1bromopro...mentioning
confidence: 99%
“…5, 29.2, 53.3, 56.6, 68.2, 79.1, 111.6, 113.3, 127.4, 130.4, 131.9, 134.7, 156.7 and 168.9. 3.65, 3.85, 3.95 (3 × 3H, 3 × s, ArOCH 3 and 2 × CO 2 CH 3 ), 4.20 (1H,dd,J 11,2,CHBr),4.85 (1H,d,J 6,OCH),4.95 (1H,d,J 6,OCH),6.85 (1H,d,J 8,ArH),7.50 (1H,dd,J 8,2,ArH),7.70 (1H,d,J 2,ArH); δ C (62.5 MHz; CDCl 3 ) 14. 2, 22.2, 30.1, 32.6, 53.3, 56.6, 60.1, 79.1, 111.2, 113.0, 128.3, 131.2, 132.6, 156.6 and 168.8.…”
Section: Dimethyl (4r5r)-2-(3-bromo-4-methoxyphenyl)-2-[(s)-1bromopro...mentioning
confidence: 99%
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“…The ORTEP drawings of the molecules of the three derivatives are shown in Fig. 1; the figure suggests that as the configurations at Cll and C12 are R,R, the configuration at C9 is S. This is the most important result obtained from the X-ray analysis as it allows the determination of the configuration of the epimer formed with higher yield in the halogenation o£ the enol ether E (Giordano, Coppi & Restelli, 1990).…”
mentioning
confidence: 94%