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Tetrahedron Letters

Volumn 20, Issue 19, 1979, Pages 1665-1668

E- and Z-vinyloxyboranes (alkenyl borinates): stereoselective formation and aldol condensation

(4) Masamune, Satoru a Mori, Sachio a Van Horn, David a Brooks, Dee W a

a MASSACHUSETTS INSTITUTE OF TECHNOLOGY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001191080 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)93618-4 Document Type: Article

Times cited : (91)

References (20)

1
- 33847088839
- For recent methods, see
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 8109
- Buse¹ Heathcock²

2
- 33947085164
- and references quoted in these articles.
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 3310
- House¹ Crumrine² Teranishi³ Olmstead⁴

3
- 84914389538
- Borverbindungen, XXXII1) An der Vinylgruppe substituierte Diäthyl(vinyloxy)borane aus Ketonen und Triäthylboran durch katalysierte Enolyse
- (1975) Justus Liebigs Annalen der Chemie , pp. 1322
- Fenzl¹ Köster²

4
- 0002192734
- (1975) Liebigs Ann. Chem. , pp. 2201
- Fenzl¹ Köster² Zimmermann³

5
- 0002978155
- (1978) Aldrichimica Acta , vol.11 , Issue.2 , pp. 23
- Masamune¹

6
- 0038405548
- 7 in 1 and 2) by direct distillation of the reaction intermediate. Heat and possibly moisture (inadvertently contaminated) might have caused partial isomerization of the originally formed E-isomer to the other.
- (1970) Tetrahedron Lett. , pp. 215
- Pasto¹ Wojtowski²

7
- 0001317550
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 5936
- Hooz¹ Linke²

8
- 0001078122
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 6891
- Hooz¹ Linke²

9
- 37049134960
- A new diketone synthesis via alkylation of bisdiazo-ketones with trialkylboranes
- Also see
- (1969) Journal of the Chemical Society D: Chemical Communications , pp. 139
- Hooz¹ Gunn²

10
- 33947300463
- Reaction of organoboranes with diazo esters and diazo ketones in the presence of deuterium oxide. A New synthesis of .alpha.-deuterio- and .alpha., .alpha.-dideuterio esters and ketones
- (1969) Journal of the American Chemical Society , vol.91 , pp. 6195
- Hooz¹ Gunn²

11
- 0003018085
- (1969) Tetrahedron Lett. , pp. 3455
- Hooz¹ Gunn²

12
- 0000481386
- Reaction of trialkylboranes with diazoacetaldehyde. A new synthesis of aldehydes
- (1970) Canadian Journal of Chemistry , vol.48 , pp. 868
- Hooz¹ Morrison²

13
- 84918339886
- R. Köster, et al., earlier showed that the Z-isomer of a vinyloxyborane undergoes a stereoselective aldol condensation in two instances.

14
- 84918339885
- The isomerization of E- to Z-vinyloxyborane could also be readily effected with catalytic amounts (0.02 equiv) of lithium t-butoxide or even with water in some cases.

15
- 84981840995
- Regel zur Abschätzung der chemischen Verschiebung von Protonen an einer Doppelbindung
- (1966) Helvetica Chimica Acta , vol.49 , pp. 164
- Pascual¹ Meier² Simon³

16
- 84918339884
- 4 to give a diastereoisomeric mixture of the diols. NMR spectra of the isopropylidine derivatives of the diols are also consistent with the assignments shown in Table 3.

17
- 84918339883
- 3) of C(3)-H of 6 or 7: 6a, δ 4.70 (d, J=8.7 Hz); 6b, δ 4.68 (d, J=7.4 Hz); 6c, δ 4.92 (d, J=7.5 Hz); 7a, δ 4.78 (d, J=6.8 Hz); 7b, δ 4.66 (d, J=6.5 Hz); 7c, δ 4.97 (d, J=5.5 Hz); 7d, δ 3.54 (ddd, J=4.7, 4.8, 8.2 Hz); 7e, δ 3.52 (dd, J=4.4, 6.5 Hz).

18
- 0000915956
- and many references quoted therein.
- (1970) J. Am. Chem. Soc. , vol.92 , pp. 714
- Brown¹ Kabalka²

19
- 84914343758
- NEW CROSS-ALDOL REACTION Via VINYLOXYBORANES
- (1976) Chemistry Letters , pp. 559
- Mukaiyama¹ Inoue²

20
- 0002246577
- NEW DIRECTED CROSS-ALDOL REACTION USING 9-TRIFLUOROMETHYLSULFONYL-9-BORABICYCLO[3.3.1]NONANE
- (1977) Chemistry Letters , pp. 153
- Inoue¹ Uchimaru² Mukaiyama³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.